108661-89-8Relevant articles and documents
Vicinal bromofluoroalkanes: Their regioselective formation and their conversion to fluoroolefins
Suga, Hiroaki,Hamatani, Takeshi,Guggisberg, Yves,Schlosser, Manfred
, p. 4255 - 4260 (1990)
The reaction of alkenes with N-bromosuccinimide and triethylamine tris(hydrofluoride) produces vic-bromofluoroalkanes (1) with high yields. As long as the addition to the double bond is sterically unhindered, bromine and fluorine get attached with very high regioselectivity, the latter halogen occupying the more substituted, carbocation stabilizing position. 2-Fluoro-1-alkenes give 1-bromo-2,2-di-fluoroalkanes (4). The heavier halogen may be removed by base promoted dehydro-fluorination, to afford fluoroolefins (2), or by reduction with tributyltin hydride, leading to mono- or difluoroalkanes (e.g., 5).
Synthesis of γ-Fluoro-α,β-unsaturated Carboxylic Esters from Saturated α-Fluoro Aldehydes
Oldendorf, Jens,Haufe, Gu?nter
, p. 52 - 57 (2007/10/03)
γ-Fluoro-α,β-unsaturated carboxylic esters 7a, 7b and 7d and 4-fluoro-4-phenylbut-3-enoic ester (8) are obtained by two alternative pathways from 2-fluoro aldehydes 5a-d, either by Horner-Wadsworth-Emmons reaction or by Wittig reaction. The aldehydes 5a-d are prepared by Swern oxidation of the corresponding fluorohydrins 4a-d. These are available from α-olefins by bromofluorination, bromine-by-acetate replacement and subsequent hydrolysis.