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Continuous-Flow Difluoromethylation with Chlorodifluoromethane under Biphasic Conditions

Continuous-Flow Difluoromethylation with Chlorodifluoromethane under Biphasic Conditions Abstract 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Flow Chemistry Springer Journals

Continuous-Flow Difluoromethylation with Chlorodifluoromethane under Biphasic Conditions

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References (45)

Publisher
Springer Journals
Copyright
2017 Akadémiai Kiadó
ISSN
2062-249X
eISSN
2063-0212
DOI
10.1556/1846.2017.00005
Publisher site
See Article on Publisher Site

Abstract

Abstract 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.

Journal

Journal of Flow ChemistrySpringer Journals

Published: Apr 1, 2017

Keywords: chemistry/food science, general; green chemistry; organic chemistry; inorganic chemistry; nanochemistry; industrial chemistry/chemical engineering

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