Trifluoromethanesulfonic acid → 5-Bromo-2-chloro-4-hydroxybenzonitrile

Participants

Reaction Steps

To a solution of 2-chloro-4-hydroxybenzonitrile (10.0 g, 65.11 mmol, Apollo Scientific) in MeCN (200 mL) was added triflic acid (6.32 mL, 71.62 mmol, Spectrochem) and NBS (13.90 g, 78.13 mmol, Spectrochem) at −30° C. The reaction mixture was allowed to warm to RT and stirred for 15 h. The reaction mixture was quenched with saturated aqueous NaHSO3 solution (500 mL) and extracted with ethyl acetate (2×1000 mL). The combined organic layers were washed with water (500 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude compound which was purified by column chromatography (silica gel 100-200 mesh and 0-6% EtOAc in hexane) to obtain 5-bromo-2-chloro-4-hydroxybenzonitrile (7.0 g, 46.2%) as white solid. m/z (ESI) 230.0 (M−H)+.

Provenance & Evidence