General method for the preparation of beta,beta-difluoroacrylates using BrF3.
Various esters were reacted with base, carbon disulfide, and methyl iodide, producing 2-carboalkoxy-1,1-bis(methyl sulfide)-1-alkenes (2). The reaction of 2 with BrF(3), followed by oxidation with HOF.CH(3)CN gave the bromodifluorosulfonyl derivatives 5. Subsequent treatment with Raney nickel led to alpha-substituted beta,beta-difluoroacrylates 6 in overall yields of 50-80%.
Hagooly
Aviv
A
School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel-Aviv University, Tel-Aviv 69978, Israel.
Rozen
Shlomo
S