Continuous photochemistry: the flow synthesis of ibuprofen via a photo-Favorskii rearrangement

被引:57
作者
Baumann, M. [1 ]
Baxendale, Ian R. [1 ]
机构
[1] Univ Durham, Dept Chem, South Rd, Durham DH1 3LE, England
关键词
ACTIVE PHARMACEUTICAL INGREDIENTS; ENABLING TECHNOLOGY; ORGANIC-SYNTHESIS; CHEMISTRY; ELECTROCHEMISTRY; ARTEMISININ; WINDOWS;
D O I
10.1039/c5re00037h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new enabling technology for performing photochemical reactions in a continuous fashion is presented. This photo-reactor is compatible with existing flow systems and can be furthermore linked to a photo-spectrometer in order to allow for real time analysis of photochemical reactions. In this communication we wish to report the profiling of this system and its application to the continuous synthesis of ibuprofen based on a photo-Favorskii rearrangement reaction of a readily available a-chloropropiophenone precursor.
引用
收藏
页码:147 / 150
页数:4
相关论文
共 33 条
[1]   Rapid Electrochemical Deprotection of the Isonicotinyloxycarbonyl Group from Carbonates and Thiocarbonates in a Microfluidic Reactor [J].
Arai, Kenta ;
Wirth, Thomas .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2014, 18 (11) :1377-1381
[2]   The synthesis of active pharmaceutical ingredients (APIs) using continuous flow chemistry [J].
Baumann, Marcus ;
Baxendale, Ian R. .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 :1194-1219
[3]   The flow synthesis of heterocycles for natural product and medicinal chemistry applications [J].
Baumann, Marcus ;
Baxendale, Ian R. ;
Ley, Steven V. .
MOLECULAR DIVERSITY, 2011, 15 (03) :613-630
[4]   Flow chemistry approaches directed at improving chemical synthesis [J].
Baxendale, Ian R. ;
Brocken, Laurens ;
Mallia, Carl J. .
GREEN PROCESSING AND SYNTHESIS, 2013, 2 (03) :211-230
[5]   The integration of flow reactors into synthetic organic chemistry [J].
Baxendale, Ian R. .
JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, 2013, 88 (04) :519-552
[6]   Synthesis of (-)-Pseudotabersonine, (-)-Pseudovincadifformine, and (+)-Coronaridine Enabled by Photoredox Catalysis in Flow [J].
Beatty, Joel W. ;
Stephenson, Corey R. J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (29) :10270-10273
[7]   The Continuous-Flow Synthesis of Ibuprofen [J].
Bogdan, Andrew R. ;
Poe, Sarah L. ;
Kubis, Daniel C. ;
Broadwater, Steven J. ;
McQuade, D. Tyler .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (45) :8547-8550
[8]  
Chirtel J. S., 1953, US Pat. US, Patent No. [2,786,045, 2786045]
[9]   [3+2]-Cycloadditions of nitrile ylides after photoactivion of vinyl azides under flow conditions [J].
Cludius-Brandt, Stephan ;
Kupracz, Lukas ;
Kirschning, Andreas .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 :1745-1750
[10]  
Elango V., 1991, US Patent, Patent No. [4,981,995, 4981995]