Diethyl Ether → 5-Bromo-2-hydroxybenzonitrile

Participants

Reaction Steps

To a stirred, cooled (−20° C.) solution of 2-cyanophenol (30 g, 252 mmole) in dried MeCN (400 mL) was added HBF4.Et2O (45 g, 277.1 mmole), and N-bromosuccinimide (53.8 g, 302.3 mmole). After addition was completed, the mixture was warmed to RT, and stirred in 4 h. The mixture was cooled and quenched by 50% aqueous NaHSO3. The mixture was concentrated to removed excess of MeCN. The off-white solid thus obtained was filtered and dried by air (42.4 g, 85%). 1H-NMR (300 MHz, DMSO-d6): δ6.99 (d, J=8.9 Hz, 1H), 7.67 (dd, J=2.5, 8.9 Hz,1H), 7.88 (d, J=2.5 Hz,1H).

Provenance & Evidence