3-Fluorophenylacetic acid → 2-(3-Fluorophenyl)ethanol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-fluorophenylacetic acid (5.0 g, 32.0 mmol) in diethyl ether (100 ml), at -10° C., was added lithium aluminium hydride (32.4 ml of a 1M solution in diethyl ether, 32.4 mmol), dropwise. The reaction mixture was allowed to warm to +25° C. and stirred for 1 h, before again cooling to -10° C., and quenching by addition of methanol (20 ml) and 4M sodium hydroxide (20 ml). The resulting slurry was filtered and the filtrate evaporated in vacuo. The crude product was chromatographed on silica gel eluting with CH2Cl2 /MeOH/NH3 (80:8:1) to give 3-(fluoro)phenethyl alcohol (3.80 g, 84%), δ (250 MHz, CDCl3) 2.87 (3H, t, J=6.5 Hz, CH2), 3.87 (3H, t, J=6.5 Hz, CH2), 6.89-7.02 (3H, m, Ar--H), 7.23-7.33 (1H, m, Ar--H).

Provenance & Evidence