2-(2-Bromo-5-chlorophenyl)acetic acid → 2-(2-Bromo-5-chlorophenyl)ethanol

Participants

Reaction Steps

A solution of 2-(2-bromo-5-chloro-phenyl)acetic acid (1.00 g, 4.01 mmol) in THF (16 mL) was cooled to 0° C. Borane-tetrahydrofuran complex (6.0 mL, 62.69 mmol) was added and the solution allowed to warm to room temperature and stirred for 3 h. Another portion of borane-tetrahydrofuran complex (6.0 mL, 62.69 mmol) was added and the reaction stirred overnight. The reaction was cooled to 0° C. and quenched by the careful addition of cold water. The aqueous was extracted with EtOAc and the organic layer washed with 2M HCl, dried (Na2SO4), and concentrated. The material was dissolved in DCM and PS-DEAM (1 g) was added and stirred overnight. The resin was filtered washing with DCM and concentrated to afford 2-(2-bromo-5-chlorophenyl)ethanol as an oil (944 mg, quant). 1H NMR (500 MHz, CDCl3) δ 7.40 (1H, d), 7.30 (1H, s), 7.00-7.03 (1H, m), 3.80-3.84 (2H, m), 2.91-2.94 (2H, m).

Provenance & Evidence