Novel method for incorporating the CHF(2) group into organic molecules using BrF(3).
2-Alkyl-1,3-dithiane derivatives, easily made from alkyl bromides and the parent 1,3-dithiane, were reacted with BrF(3) to form the corresponding 1,1-difluoromethyl alkanes (RCHF(2)) 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.
Sasson
Revital
R
School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel-Aviv University, Tel-Aviv 69978, Israel.
Hagooly
Aviv
A
Rozen
Shlomo
S