2,4,5-Trifluorophenylacetic acid → 2-(2,4,5-Trifluorophenyl)ethan-1-ol

Participants

Reaction Steps

A solution of 2-(2,4,5-trifluorophenyl)acetic acid (1 g, 5.26 mmol) in dry THF (20 mL) was carefully added over 2 min to solution of 2M LAH (10.52 mL, 10.52 mmol) at 0° C. The reaction mixture was allowed to warm to rt and was stirred for 6 h. The reaction was quenched with 0.5 mL of water (stir for 10 min), 0.5 mL of 15% NaOH/water (stir for 10 min), and then 1.0 mL of water. After stirring for 18 h, the mixture was filtered through celite. The filtrate was concentrated in vacuum. The residue was dried under high vacuum for 16 h to afford 2-(2,4,5-trifluorophenyl)ethanol (850 mg, 4.83 mmol, 92% yield) as a clear viscous oil, which was used as is in the next step without further purification. 1H NMR (500 MHz, CDCl3) δ 7.11 (ddd, J=10.3, 8.7, 7.2 Hz, 1H), 6.93 (td, J=9.7, 6.6 Hz, 1H), 3.87 (t, J=6.5 Hz, 2H), 2.88 (t, J=6.5 Hz, 2H).

Provenance & Evidence