Ibuprofen Goes With The Flow | October 19, 2009 Issue - Vol. 87 Issue 42 | Chemical & Engineering News
Volume 87 Issue 42 | p. 37 | Concentrates
Issue Date: October 19, 2009

Ibuprofen Goes With The Flow

Continuous-flow synthesis shows the way to safer, cheaper, and more efficient production of common painkiller
Department: Science & Technology
Keywords: ibuprofen, continuous flow, microreactor
8742scon_ibuprofen
 

Using a three-step continuous-flow process, chemists at Florida State University have prepared the popular nonsteroidal anti-inflammatory drug ibuprofen (Angew. Chem. Int. Ed., DOI: 10.1002/anie.200903055). Such continuous-flow syntheses could lead to safer, cheaper, and more efficient pharmaceutical production, according to D. Tyler McQuade and Andrew R. Bogdan, who spearheaded the work. Their synthesis makes use of a simplified microreactor—a device in which reactions are carried out in microchannels or narrow-bore tubing. The system gives chemists precise control over heat transfer and mixing and also eliminates the need to purify any intermediates. To make ibuprofen, McQuade and Bogdan’s team had to design a reaction sequence in which all excess reagents and by-products were compatible with downstream reactions. Their scheme begins with a Friedel-Crafts acylation of isobutylbenzene, followed by a 1,2-aryl migration, and concludes with a saponification. With less than 500 cm of tubing and five syringe pumps, the chemists were able to produce crude ibuprofen at a rate of 9 mg/minute. They note that a continuous, high-throughput synthesis of the drug could be easily achieved by adding parallel reactors or by lengthening the channels combined with alternative pumping mechanisms.

 
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