Novel Method for Incorporating the CHF2 Group into Organic Molecules Using BrF3

Revital Sasson, Aviv Hagooly, and Shlomo Rozen*
School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel-Aviv University, Tel-Aviv 69978, Israel
Org. Lett., 2003, 5 (5), pp 769–771
DOI: 10.1021/ol034051n
Publication Date (Web): February 12, 2003
Copyright © 2003 American Chemical Society
*

 Fax:  +972 3 6409293.

, rozens@post.tau.ac.il

Abstract

Abstract Image

2-Alkyl-1,3-dithiane derivatives, easily made from alkyl bromides and the parent 1,3-dithiane, were reacted with BrF3 to form the corresponding 1,1-difluoromethyl alkanes (RCHF2) in 60−75% yield. The reaction proceeds well with primary alkyl halides. The limiting step for secondary alkyl halides is the relatively low yield of the dithiane preparation. The two sulfur atoms of the dithiane are essential for the reaction.

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History

  • Published In Issue March 06, 2003
  • Received January 11, 2003

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