Hydrochloric Acid → 2-(4-Fluorophenyl)propan-1-ol

Participants

Reaction Steps

To a solution of 2-(4-fluorophenyl)propanoic acid (1 g, 5.95 mmol) in THF (20 mL) at 0° C. was added 1M BH3.THF (11.89 mL, 11.89 mmol) in THF and the resulting mixture was stirred at room temp for 3 h. Then, 1N HCl (3 mL) was added and the mixture was extracted with ethyl acetate 100 mL), washed with brine (50 mL), dried (Na2SO4), filtered and concentrated. The residue was then purified by Biotage (5-50% EtOAc/hexane) to afford 2-(4-fluorophenyl)propan-1-ol (300 mg, 1.946 mmol, 32.7% yield) as colorless oil. 1H NMR (500 MHz, CDCl3) δ 7.23 (dd, J=8.5, 5.5 Hz, 2H), 7.04 (t, J=8.7 Hz, 2H), 3.79-3.63 (m, 2H), 2.97 (sxt, J=6.9 Hz, 1H), 1.34 (t, J=5.5 Hz, 1H), 1.29 (d, J=7.1 Hz, 3H).

Provenance & Evidence