Dibromodifluoromethane → Benzyl 8,8-difluoro-7-methyl-7-octenoate

Reaktionsgleichung

CN(P(N(C)C)N(C)C)C.Br[C:12](Br)([F:14])[F:13].O=[C:17]([CH3:33])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>COCCOCCOC>[F:13][C:12]([F:14])=[C:17]([CH3:33])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:24]

Komponenten

Versuchsvorschrift

123 ml (0.68 mol) Tris(dimethylamino)phosphine in 100 ml diglyme was added slowly dropwise to a solution of 26.3 ml (0.34 mol) dibromodifluoromethane in 800 ml diglyme. After stirring for one hour on an ice bath, 43 g (0.17 mol}benzyl 7-oxooctanoate in 100 ml diglyme was slowly added dropwise. The ice bath was removed and the reaction mixture stirred for 40 minutes at room temperature, poured into 1 liter ice-water and extracted with ether. The ether phase was washed twice with water, dried over sodium sulphate, filtered and concentrated. The residue was purified by column chromatography (silica gel hexane/ether=3:1)