The Journal of organic chemistry

A Novel Method for the Preparation of α, α'-Difluoroesters and Acids Using BrF3

A Hagooly, R Sasson, S Rozen

Index: Hagooly, Aviv; Sasson, Revital; Rozen, Shlomo Journal of Organic Chemistry, 2003 , vol. 68, # 21 p. 8287 - 8289

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Citation Number: 26

Abstract

Alkyl-, haloalkyl-, and ketoalkyl-2-ethoxycarbonyl-1, 3-dithianes were easily made from the appropriate primary or secondary alkyl bromides, 1, 3-dithiane, and ethyl chloroformate. They were reacted with BrF3 to form the corresponding α, α-difluoro esters in 65-75% yield. Reaction conditions are very mild (1-2 min, 0° C). The two sulfur atoms of the dithiane are essential for the reaction.