Sodium Carbonate → 1-Benzyl-3-(3,4-difluorophenyl)pyrrolidin-3-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-bromo-3,4-difluorobenzene (5.0 g, 25.9 mmol) in dry diethyl ether (40 mL), under nitrogen, was added dropwise at −78° C., n-butyllithium (2.5 M in hexane, 10.36 mL, 25.9 mmol). The mixture was stirred for 1 h after which a solution of 1-benzylpyrrolidin-3-one (3.63 g, 20.7 mmol) in dry diethyl ether (20 mL) was added drop wise. The resulting mixture was stirred for 1 h at −78° C. and then brought to ambient temperature. Aqueous sodium carbonate (10%, 50 mL) was added and the aqueous phase was extracted with ethyl acetate (3×50 mL). The combined organic phase was washed with brine, dried (MgSO4) and evaporated. Purification by flash column chromatography on silica gel (ethyl acetate/isooctane, 1:1) gave the title compound (3.6 g). MS m/z (rel. intensity, 70 eV) 289 (M+, 3), 198 (74), 133 (44), 132 (38), 91 (bp).

Provenance & Evidence