Nitrogen → 2-[2-(3-Bromophenyl)ethoxy]ethanol

Participants

Reaction Steps

A 100 mL three-necked flask was fitted with a dropping funnel, septa and a N2 balloon. The flask was charged with a solution of 2-(3-bromophenethoxy)acetic acid (2.20 g, 8.49 mmol) in anhydrous THF (20 mL) and cooled in an ice bath. Borane-THF complex (1.0 M in THF, 17 mL, 2 equiv.) was added dropwise to the solution of the starting material in 15 min. After 3 h, the reaction was quenched by addition (cautiously at first until H2 evolution has abated) of THF/H2O (1:1, 30 mL). The resulting mixture was an amber solution together with a colorless precipitate. THF was removed from the solution by partial evaporation, and the product was extracted into ether (200 mL). The organic phase was washed sequentially with water (20 mL) and brine (20 mL), evaporated, and dried over Na2SO4 to afford the title product (2.00 g, 96%) as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 7.40 (s, 1H), 7.35-7.39 (m, 1H), 7.17-7.22 (m, 2H), 3.70-3.75 (m, 4H), 3.58 (t, 2H, J=6.9 Hz), 2.90 (t, 2H, J=7.2 Hz).

Provenance & Evidence