4,5-Difluoro-2-methoxyphenylacetic acid → 2-(4,5-Difluoro-2-methoxyphenyl)ethan-1-ol

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Reaction Conditions

Reaction Steps

To a solution of 2-(4,5-difluoro-2-methoxyphenyl)acetic acid (1 g, 4.95 mmol) in THF (20 mL) at 0° C. was added 1M LAH (9.89 mL, 9.89 mmol) in THF and the resulting mixture was heated at 60° C. for 3 h. Mixture was then cooled and quenched with dropwise addition of water (0.5 mL), 1N NaOH (0.5 mL), and then 1 mL H2O. After stirring for 15 min. the mixture was filtered through celite. The filtrate was concentrated in vacuo. The residue was dried under high vacuum to afford 2-(4,5-difluoro-2-methoxyphenyl)ethanol (800 mg, 4.25 mmol, 86% yield) as a clear viscous oil. Used as is in the next step without further purification. 1H NMR (500 MHz, CDCl3) δ 7.02 (t, J=9.8 Hz, 1H), 6.71 (dd, J=12.1, 6.7 Hz, 1H), 3.87-3.82 (m, 2H), 3.81 (s, 3H), 2.85 (t, J=6.5 Hz, 2H), 1.56 (br. s., 1H).

Provenance & Evidence