Sodium hydride → 4-Bromo-2-hydroxybenzonitrile

Participants

Reaction Steps

To a stirred solution of 4-bromo-2-fluorobenzonitrile (4.0 g, 20 mmol) in DMF (20 mL) was added 2-(methylsulfonyl)ethanol (3.7 g, 30 mmol) and then NaH (2.4 g, 60% in mineral, 60 mmol) in portions at 0° C. The mixture was then warmed to rt. and quenched with 1N HCl, and extracted by EtOAc. The organic layers were washed with brine and dried over sodium sulfate, concentrated to give 4-bromo-2-hydroxybenzonitrile. 1H-NMR (400 MHz, DMSO) δ 7.55-7.57 (d, J=8.61 Hz, 1H), 7.16 (s, 1H), 7.11-7.13 (m, 1H).

Provenance & Evidence