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

Temperature

-10 °C

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).

1. temperatureto warm to +25° C.
2. customquenching by addition of methanol (20 ml) and 4M sodium hydroxide (20 ml)
3. filtrationThe resulting slurry was filtered
4. customthe filtrate evaporated in vacuo
5. customThe crude product was chromatographed on silica gel eluting with CH2Cl2 /MeOH/NH3 (80:8:1)

ORD record

ord-187348cfae7f4dfb8d902037ae93ca7e

Source dataset

uspto-grants-1999_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05889008