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Search for "flow reactor" in Full Text gives 110 result(s) in Beilstein Journal of Organic Chemistry.

Continuous flow photocyclization of stilbenes – scalable synthesis of functionalized phenanthrenes and helicenes

  • Quentin Lefebvre,
  • Marc Jentsch and
  • Magnus Rueping

Beilstein J. Org. Chem. 2013, 9, 1883–1890, doi:10.3762/bjoc.9.221

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  • backbone functionalized phenanthrenes and helicenes of various sizes in good yields. Keywords: continuous-flow reactor; flow chemistry; helicenes; light-driven cyclization reaction; photocyclization; stilbenes; Introduction Phenanthrenes are versatile intermediates toward polycyclic aromatic hydrocarbons
  • ) could be converted to phenanthrene (2a) in 95% NMR yield with a retention time of 83 min (Table 1, entry 5). The flow-reactor setup used for the optimization (Table 1) is shown in Figure 1. UV-transparent ethylene propylene copolymer capillary (FEP, outer/inner diameter 1/0.5 mm, total volume 5 mL) was
  • substitution patterns are obtained in good to excellent yields. In addition our first attempts to scale up the flow photocyclization reactions were successful providing the opportunity for multi-gram syntheses. Flow-reactor setup used in the optimization study. Photocyclization of stilbene to phenanthrene
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Published 17 Sep 2013

Raman spectroscopy as a tool for monitoring mesoscale continuous-flow organic synthesis: Equipment interface and assessment in four medicinally-relevant reactions

  • Trevor A. Hamlin and
  • Nicholas E. Leadbeater

Beilstein J. Org. Chem. 2013, 9, 1843–1852, doi:10.3762/bjoc.9.215

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  • to the flow unit In interfacing our Raman spectrometer with a continuous-flow reactor, our objective was to use a similar approach to that which proved successful when using microwave heating. Borosilicate glass is essentially “Raman transparent”. Therefore reactions could be monitored by placing a
  • the spectrometer almost without any loss of light. The optimum distance of the light-pipe to the outside wall of the reaction vessel was found to be approximately 0.5 mm. Moving to our continuous-flow reactor, we decided to place the spectroscopic interface just after the back-pressure regulator
  • activity in this area. As a result, we chose to monitor the 1608 cm−1 signal. To mimic a product mixture, we pumped a solution of 1 in acetone through our flow reactor, intercepted it with an equal volume of ethyl acetate and passed this mixture through the flow cell. We recorded a Raman spectrum every 15
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Published 11 Sep 2013

[3 + 2]-Cycloadditions of nitrile ylides after photoactivation of vinyl azides under flow conditions

  • Stephan Cludius-Brandt,
  • Lukas Kupracz and
  • Andreas Kirschning

Beilstein J. Org. Chem. 2013, 9, 1745–1750, doi:10.3762/bjoc.9.201

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  • transformations well above the boiling point of the solvent, and this was secured by placing a backpressure regulator behind the flow system. In contrast, the photochemical flow-reactor was composed of a Teflon (FEP) tubing (volume: 3.0 mL, inner diameter = 0.75 mm) and a Pyrex filter. These were placed onto the
  • continuously in good yields under thermal as well as under photochemical conditions in appropriate flow reactor devices (Table 1). Complete conversion was achieved at 190 °C after 1 min in dichloromethane. At higher temperatures as well as at reduced flow rates the amount of decomposition products increased
  • . The photochemical transformation required longer reaction times, but the products were formed under thermally mild conditions in improved yields and with higher purity. Therefore, we decided to continue our studies with the photochemical flow-reactor and to extend these studies to the photoinduced
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Published 26 Aug 2013

The rapid generation of isothiocyanates in flow

  • Marcus Baumann and
  • Ian R. Baxendale

Beilstein J. Org. Chem. 2013, 9, 1613–1619, doi:10.3762/bjoc.9.184

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  • (benzyldimethylamine resin) and SiO2-pyr. The latter allowed for the isolation of the desired isothiocyanate in high yield and with very little contamination by the furoxan byproduct. We translated the outcome of these preliminary results into a flow protocol using a commercially available Vapourtec R series flow
  • reactor [56] which was operated with MeCN as the system solvent. Stock solutions of the chloroxime starting materials were prepared in the same solvent (0.25–0.5 M) and injected into a sample loop (2–10 mL size). Both the solid supported base (SiO2-pyr) and immobilised thiourea species (QP-TU or QS-MTU
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Published 08 Aug 2013

Controlled synthesis of poly(3-hexylthiophene) in continuous flow

  • Helga Seyler,
  • Jegadesan Subbiah,
  • David J. Jones,
  • Andrew B. Holmes and
  • Wallace W. H. Wong

Beilstein J. Org. Chem. 2013, 9, 1492–1500, doi:10.3762/bjoc.9.170

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  • optimization of large area devices is costly and often impossible to achieve. Continuous-flow synthesis enables straight-forward scale-up of materials compared to conventional batch reactions. In this study, poly(3-hexylthiophene), P3HT, was synthesized in a bench-top continuous-flow reactor. Precise control
  • -grade P3HT using continuous-flow methods with simple benchtop equipment. Conclusion P3HT has been successfully synthesized in continuous flow by using a commercially available benchtop flow reactor. After optimization of reaction conditions, good molecular-weight control was achieved by adjusting the
  • , the P3HT samples synthesized in flow showed comparable regioregularity to samples from batch synthesis. The telescoped flow synthesis of P3HT from 2,5-dibromo-3-hexylthiophene (1) was also achieved on the benchtop flow reactor. Finally, BHJ solar cells containing flow-synthesized P3HT showed
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Published 25 Jul 2013

Hypervalent iodine/TEMPO-mediated oxidation in flow systems: a fast and efficient protocol for alcohol oxidation

  • Nida Ambreen,
  • Ravi Kumar and
  • Thomas Wirth

Beilstein J. Org. Chem. 2013, 9, 1437–1442, doi:10.3762/bjoc.9.162

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  • in combination with a catalytic amount of TEMPO have already been reported in highly selective oxidations of alcohols to carbonyl compounds [14]. The development of efficient flow-reactor systems for molecular transformations is an important area in organic synthesis. The introduction of more general
  • time of 4.5 min. The reaction mixture exiting the flow reactor was quenched with water and, after completion of the reaction, extracted with CH2Cl2. The combined organic layers were dried over magnesium sulfate and the solvents were removed in vacuo. Direct analysis with GC allowed the determination of
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Published 17 Jul 2013

Camera-enabled techniques for organic synthesis

  • Steven V. Ley,
  • Richard J. Ingham,
  • Matthew O’Brien and
  • Duncan L. Browne

Beilstein J. Org. Chem. 2013, 9, 1051–1072, doi:10.3762/bjoc.9.118

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  • early stages of development were heavily influenced by a consideration of the potential for automated visual monitoring, and indeed this visual monitoring technique co-evolved with the gas-flow reactor as we assessed different gases and their potential reactivity in continuous flow processes. The
  • passing through the gas-flow reactor a flow stream of dichloromethane containing a red dye was allowed to degas in a lower pressure environment. A camera mounted over a flat tubing array captured images of the resulting biphasic system. The images were automatically filtered to locate the areas of
  • reactions involving a colour change can be monitored simultaneously. The use of a solid-state CCD imager reduces the number of moving parts, which should improve the overall reliability of the device. Simple colour-change experiments to assess a new AF-2400 gas permeable flow reactor. The reactor consists
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Published 31 May 2013

3D-printed devices for continuous-flow organic chemistry

  • Vincenza Dragone,
  • Victor Sans,
  • Mali H. Rosnes,
  • Philip J. Kitson and
  • Leroy Cronin

Beilstein J. Org. Chem. 2013, 9, 951–959, doi:10.3762/bjoc.9.109

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  • connected with a length of tubing with a volume 0.1 mL to the IR flow cell. Hence, the total flow reactor volume (VR) was 0.5 mL. The syntheses of the imines were monitored by an in-line ATR-IR flow cell and were conducted at a total flow rate of 0.25 mL min−1, where two equimolar methanolic solutions of 1
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Published 16 May 2013

Flow photochemistry: Old light through new windows

  • Jonathan P. Knowles,
  • Luke D. Elliott and
  • Kevin I. Booker-Milburn

Beilstein J. Org. Chem. 2012, 8, 2025–2052, doi:10.3762/bjoc.8.229

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  • whilst little selectivity (55:45) was achieved in batch for the same conversion. Increasing the width of the channel in the flow reactor allowed flow rates to be increased whilst retaining this level of selectivity; however, productivity even with this larger reactor was still extremely low (0.014 mmol/h
  • anthelmintic asaridole (23, Scheme 8) [32]. Comparison of this microflow reaction to a batch reaction using a 500 W tungsten lamp showed that although the microflow reaction gave a higher yield (85% versus 67%), the productivity of the flow reactor was markedly lower (1.5 mg/h versus 175 mg/h). This highlights
  • flow-reactor light source was employed in the batch reactor, a substantial decrease in conversion was observed in the same time period (0.54 versus 0.16 mmol/h). Whilst this remains 7.5 times greater than the flow reaction, the sense of sacrificing conversion for productivity would depend on a number
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Published 21 Nov 2012

Photochemistry with laser radiation in condensed phase using miniaturized photoreactors

  • Elke Bremus-Köbberling,
  • Arnold Gillner,
  • Frank Avemaria,
  • Céline Réthoré and
  • Stefan Bräse

Beilstein J. Org. Chem. 2012, 8, 1213–1218, doi:10.3762/bjoc.8.135

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  • : Description of the flow reactor setup, kinetics, experimental procedures and spectroscopic data of all compounds. Acknowledgements We thank the Fonds der Chemischen Industrie for financial support.
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Published 31 Jul 2012

Continuous-flow hydration–condensation reaction: Synthesis of α,β-unsaturated ketones from alkynes and aldehydes by using a heterogeneous solid acid catalyst

  • Magnus Rueping,
  • Teerawut Bootwicha,
  • Hannah Baars and
  • Erli Sugiono

Beilstein J. Org. Chem. 2011, 7, 1680–1687, doi:10.3762/bjoc.7.198

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  • of α,β-unsaturated ketones starting from alkynes and aldehydes by employing a heterogeneous catalyst in a flow microwave. The procedure presents a straightforward and convenient access to valuable differently substituted chalcones and can be applied on multigram scale. Keywords: chalcones; flow
  • reactor; green chemistry; heterogeneous catalysis, microwave; Introduction In recent years, the development of continuous-flow technologies has expanded considerably and has had a significant impact on modern organic synthetic chemistry. Continuous-flow processes offer advantages, such as operational
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Published 15 Dec 2011

Continuous proline catalysis via leaching of solid proline

  • Suzanne M. Opalka,
  • Ashley R. Longstreet and
  • D. Tyler McQuade

Beilstein J. Org. Chem. 2011, 7, 1671–1679, doi:10.3762/bjoc.7.197

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  • attributes of micro- and mesoflow reactors, the continuous use of solids remains challenging. The introduction of solids to a flow reactor is particularly difficult as most pumps function poorly with even small particulates, which in turn can result in channel clogging. Although the use of solids in flow has
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Published 14 Dec 2011

Continuous-flow enantioselective α-aminoxylation of aldehydes catalyzed by a polystyrene-immobilized hydroxyproline

  • Xacobe C. Cambeiro,
  • Rafael Martín-Rapún,
  • Pedro O. Miranda,
  • Sonia Sayalero,
  • Esther Alza,
  • Patricia Llanes and
  • Miquel A. Pericàs

Beilstein J. Org. Chem. 2011, 7, 1486–1493, doi:10.3762/bjoc.7.172

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  • polymer. With the most efficient resin (1a), ca. 30 mmol of product was isolated per mmol of resin for every flow experiment (5 h), thus meaning a four-fold improvement with respect to the batch process. Conclusion In summary, a packed-bed continuous-flow reactor was designed and implemented, based on
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Published 31 Oct 2011

Coupled chemo(enzymatic) reactions in continuous flow

  • Ruslan Yuryev,
  • Simon Strompen and
  • Andreas Liese

Beilstein J. Org. Chem. 2011, 7, 1449–1467, doi:10.3762/bjoc.7.169

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  • in a cascade of two CSTRs, whose kinetic behavior approximates an optimum for this reaction system in a plug-flow reactor. In this way the authors were able to reach 95% conversion with a space-time yield of 28 g L−1 day−1 and an enzyme consumption of 0.9 U g−1. The reactor cascade was stably
  • continuous synthesis of the neolignan natural product grossamide (52) by a two-step chemo-enzymatic reaction cascade starting from ferulic acid (49) and tyramine (50) (Scheme 15). The synthesis was performed in a fully automated flow reactor consisting of three types of prepacked columns. The first two
  • scavenger column containing a sulfonic acid resin. The H2O2-mediated oxidative dimerization and intramolecular cyclization of 51 to the product 52 was catalyzed by an immobilized peroxidase enzyme packed into the last column. The authors validated the design of the flow reactor by synthesizing gram
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Published 24 Oct 2011

Multistep flow synthesis of vinyl azides and their use in the copper-catalyzed Huisgen-type cycloaddition under inductive-heating conditions

  • Lukas Kupracz,
  • Jan Hartwig,
  • Jens Wegner,
  • Sascha Ceylan and
  • Andreas Kirschning

Beilstein J. Org. Chem. 2011, 7, 1441–1448, doi:10.3762/bjoc.7.168

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  • reactor. Keywords: flow reactor; inductive heating; iodine azide; polymer-supported reagents; vinyl azides; Introduction Azides are highly versatile organic functional groups and their preparation and their reactivity are well explored [1]. In contrast, the synthesis of vinyl azides is far away from
  • ] or copper-on-charcoal (Cu/C) [30], can serve as a catalytic source that promotes the CuAAC. Bogdan et al. combined this observation with flow technology by using a custom-made heated copper flow reactor [31]. We successfully implemented the CuAAC by inductively heating copper wire inside a flow
  • under flow conditions A glass reactor (12 cm length and 8.5 mm internal diameter) filled with polymer-bound iodate(I) complex 5 (5 g; theoretical loading = 3.5 mmol/g) and a second identical flow reactor, which was filled with a slurry of polystyrene-bound 1,8-diaza-[5.4.0]bicyclo-7-undecene (8) (4 g
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Published 20 Oct 2011

Continuous preparation of carbon-nanotube-supported platinum catalysts in a flow reactor directly heated by electric current

  • Alicja Schlange,
  • Antonio Rodolfo dos Santos,
  • Ulrich Kunz and
  • Thomas Turek

Beilstein J. Org. Chem. 2011, 7, 1412–1420, doi:10.3762/bjoc.7.165

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  • preparation in a flow reactor which could be used at a large scale. Keywords: carbon nanotubes; continuous catalyst synthesis; direct electrical heating; flow reactors; fuel cell platinum catalyst; Introduction Batch processes represent the state of the art in catalyst preparation. One reason for employing
  • products in a continuous operation mode attractive. On the one hand numerous organic reactions have been described in the flow mode [1][2][3][4][5][6][7][8][9][10][11]. On the other hand the preparation of catalysts in a continuously operated flow reactor is still a research field with only a few published
  • demonstrate, for the first time, a simple and cost-effective method for the preparation of carbon-nanotube-supported Pt catalysts by using a continuously operated tubular flow reactor. The heating concept was realized by passing electrical current directly through the reactor wall. The experimental setup is
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Published 14 Oct 2011

Translation of microwave methodology to continuous flow for the efficient synthesis of diaryl ethers via a base-mediated SNAr reaction

  • Charlotte Wiles and
  • Paul Watts

Beilstein J. Org. Chem. 2011, 7, 1360–1371, doi:10.3762/bjoc.7.160

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  • (Scheme 2) was investigated under continuous-flow conditions. As the continuous-flow reactor enables the reaction chamber to be maintained at the reaction temperature (once the steady state is reached) time is not wasted for heating and cooling of the stopped-flow “batches”. Consequently, the system has
  • required in flow when compared to the microwave methodology can be rationalised if you think that part of the reaction time for a microwave reaction involves the heating up and cooling down of the system, and it is this increase in processing time that is removed by a flow reactor once it has reached
  • Moseley [15], the use of a flow reactor meant that it was possible to optimise the reaction of 4-cyanophenol (9) to obtain 2-chloro-1-(4-cyanophenoxy)-4-nitrobenzene (13) in >99% yield, compared with 42% in the microwave reactor. Use of inorganic bases: Whilst the use of organic bases enabled a comparison
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Published 04 Oct 2011

Efficient and selective chemical transformations under flow conditions: The combination of supported catalysts and supercritical fluids

  • M. Isabel Burguete,
  • Eduardo García-Verdugo and
  • Santiago V. Luis

Beilstein J. Org. Chem. 2011, 7, 1347–1359, doi:10.3762/bjoc.7.159

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  • conversion and enantioselectivity were produced upon changing the solvent from scCO2 to scC2H6 working at 30 °C and 10 MPa, in a flow reactor at 4.3 mmol·min–1 (Scheme 1). The poor performance of scCO2 was related to the partial catalyst poisoning due to the formation of CO through a water-shift reaction
  • low stability of the active species in the absence of the substrate and this could be avoided or minimized by continuous operation in a flow reactor. Thus, more than 60 h of operation time could be achieved moving from batch to continuous flow. Finally, the remaining examples concern our own work on
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Published 30 Sep 2011

Scaling up of continuous-flow, microwave-assisted, organic reactions by varying the size of Pd-functionalized catalytic monoliths

  • Ping He,
  • Stephen J. Haswell,
  • Paul D. I. Fletcher,
  • Stephen M. Kelly and
  • Andrew Mansfield

Beilstein J. Org. Chem. 2011, 7, 1150–1157, doi:10.3762/bjoc.7.133

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  • reactor. The Pd-supported silica monolith flow reactor was then placed into the microwave cavity and connected to an HPLC pump and a backpressure regulator to minimize the formation of gas bubbles. The flow rate and microwave power were varied to optimize the reactant contact time and temperature
  • comparable pore diameters and surface areas, were fabricated with diameters of 3.2 and 6.4 mm to give volumetric capacities of 0.205 and 0.790 mL, respectively. The two monoliths were functionalized with a loading of 4.5 wt % Pd and then sealed in heat-shrinkable Teflon® tubing to form a monolithic flow
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Published 23 Aug 2011

Evaluation of a commercial packed bed flow hydrogenator for reaction screening, optimization, and synthesis

  • Marian C. Bryan,
  • David Wernick,
  • Christopher D. Hein,
  • James V. Petersen,
  • John W. Eschelbach and
  • Elizabeth M. Doherty

Beilstein J. Org. Chem. 2011, 7, 1141–1149, doi:10.3762/bjoc.7.132

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  • a convenient bench-top hydrogen flow reactor, the H-Cube®, designed for smaller-scale use in academic and drug discovery labs [6]. The reactor features a built-in hydrogen generator that functions by the electrolysis of water. Disposable pre-packed catalyst cartridges (CatCart®) are also available
  • results will be the subject of future reports. Experimental Instrument set up SAH3 reactor configuration. A standard H-Cube® hydrogenation flow reactor (ThalesNano Technology, Inc., Budapest, Hungary) was adapted to allow for fixed-loop injections and real-time monitoring by UV. The schematic is shown in
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Published 22 Aug 2011

Continuous flow photolysis of aryl azides: Preparation of 3H-azepinones

  • Farhan R. Bou-Hamdan,
  • François Lévesque,
  • Alexander G. O'Brien and
  • Peter H. Seeberger

Beilstein J. Org. Chem. 2011, 7, 1124–1129, doi:10.3762/bjoc.7.129

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  • reaction conditions using the flow reactor allowed minimization of secondary photochemical reactions. Keywords: azepinones; azides; continuous flow; nitrenes; photochemistry; Findings Although photochemical rearrangements are an important class of reactions for heterocycle synthesis [1][2], their use is
  • . General conditions for the photolysis of aryl azides in continuous flow. Effect of aryl azide concentration on conversion. 3H-azepinone derivatives prepared by photolysis of aryl azides in continuous flow. Supporting Information Supporting Information File 188: Description of the flow reactor setup
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Published 17 Aug 2011

A practical microreactor for electrochemistry in flow

  • Kevin Watts,
  • William Gattrell and
  • Thomas Wirth

Beilstein J. Org. Chem. 2011, 7, 1108–1114, doi:10.3762/bjoc.7.127

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  • 1,2-diphenylethane (7a) were obtained with the device depicted in Figure 1; the reactions are shown in Scheme 3. The Kolbe reaction did not seem to be a very suitable reaction for a flow reactor due to the large amount of carbon dioxide and hydrogen that is formed at the anode during the
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Published 15 Aug 2011

Continuous gas/liquid–liquid/liquid flow synthesis of 4-fluoropyrazole derivatives by selective direct fluorination

  • Jessica R. Breen,
  • Graham Sandford,
  • Dmitrii S. Yufit,
  • Judith A. K. Howard,
  • Jonathan Fray and
  • Bhairavi Patel

Beilstein J. Org. Chem. 2011, 7, 1048–1054, doi:10.3762/bjoc.7.120

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  • : continuous flow reactions; fluorine; fluoropyrazole; gas-liquid flow reactor; selective direct fluorination; Introduction Organic systems which bear fluorine atoms are used in an ever widening range of applications in the life sciences. Many commercially significant pharmaceutical and agrochemical products
  • /liquid–liquid/liquid continuous flow process. No examples of gas/liquid–liquid/liquid processes involving direct fluorination as the first stage of a continuous flow procedure have been reported previously. Results and Discussion After some development work, a continuous flow reactor for sequential gas
  • 1.2 mmol of hydrazine hydrate (3a) was also dissolved in 4 mL of solvent (either acetonitrile, ethanol or water). Both were added concurrently to the flow reactor at the rate of 2 mL/min into Inputs B and C, respectively, using accurate syringe pumps. Excess 10% F2/N2 gas mixture was passed into the
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Published 02 Aug 2011

Chemistry in flow systems II

  • Andreas Kirschning

Beilstein J. Org. Chem. 2011, 7, 1046–1047, doi:10.3762/bjoc.7.119

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  • , which are difficult to handle in a batch reactor. And third, new heating concepts, including inductive heating, are rendered possible, allowing us to carry out accelerated synthesis under pressure, up to supercritical conditions, but whereby only a small volume of the reaction mixture inside the flow
  • reactor is exposed to these extreme conditions. You are invited to explore this Thematic Series and you will see contributions from some of the most prominent and creative groups in the world working in the field of flow chemistry. Not surprisingly this series has significantly increased in size since the
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Published 02 Aug 2011

Continuous flow hydrogenation using polysilane-supported palladium/alumina hybrid catalysts

  • Hidekazu Oyamada,
  • Takeshi Naito and
  • Shū Kobayashi

Beilstein J. Org. Chem. 2011, 7, 735–739, doi:10.3762/bjoc.7.83

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  • continuous flow reactor and an image of the top of the column are shown in Figure 1. A high performance liquid chromatography (HPLC) pump was used to feed the substrate into the central hole in the top of the column, which was filled with the Pd/(PSi–Al2O3) catalyst. Hydrogen gas was introduced into the six
  • leaching was detected (ICP). Further studies of the application of these systems to large-scale production are now in progress. Experimental The continuous flow reactor system comprised the following devices (Figure 1): HPLC pump: Shimadzu LC-6AD or Eyela 301. Mass flow controller: Lyntec MC-3000E and RP
  • , CDCl3) δ 7.46–7.50 (m, 2H), 7.60–7.63 (m, 1H), 8.12–8.14 (m, 2H). Schematic diagram of the continuous flow reactor (left) and the column top (right). Hydrogenation of ethyl cinnamate. Hydrogenation of trans-stilbene and trans-chalcone. Hydrogenation of nitrobenzene and deprotection of the Cbz group
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Published 31 May 2011
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