Authors:
Bernhard GutmannNAWI Graz, Heinrichstrasse 28, A-8010 Graz, Austria
Research Center Pharmaceutical Engineering GmbH (RCPE), Inffeldgasse 13, 8010 Graz, Austria

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Paul HanselmannLonza AG, CH-3930 Visp, Switzerland

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Michael BersierLonza AG, CH-3930 Visp, Switzerland

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Dominique RobergeLonza AG, CH-3930 Visp, Switzerland

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C. Oliver KappeNAWI Graz, Heinrichstrasse 28, A-8010 Graz, Austria
Research Center Pharmaceutical Engineering GmbH (RCPE), Inffeldgasse 13, 8010 Graz, Austria

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Herein, we present the development of a continuous-flow process for a difluoromethylation with difluorocarbene as the reactive reagent. The difluoromethylated product is a key intermediate during the synthesis of eflornithine, a pharmaceutical that is on the World Health Organization’s Model List of Essential Medicines. The developed procedure uses inexpensive and commercially available chlorodifluoromethane (CHF2Cl, Freon 22) as difluorocarbene source. Deprotonation of CHF2Cl with NaOH in a biphasic mixture of organic solvent-water generates the carbene. A fast subsequent reaction of the difluorocarbene with the substrate generates the desired product with excellent selectivity.

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Journal of Flow Chemistry
Language English
Size A4
Year of
Foundation
2011
Volumes
per Year
1
Issues
per Year
4
Founder Áramlásos Kémiai Tudományos Társaság
Founder's
Address
H-1031 Budapest, Hungary Záhony utca 7.
Publisher Akadémiai Kiadó
Springer Nature Switzerland AG
Publisher's
Address
H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
CH-6330 Cham, Switzerland Gewerbestrasse 11
Responsible
Publisher
Chief Executive Officer, Akadémiai Kiadó
ISSN 2062-249X (Print)
ISSN 2063-0212 (Online)