2-Hydroxybenzonitrile → 2-Hydroxy-5-iodo-benzonitrile

Participants

Reaction Conditions

Reaction Steps

CF3SO3H (40 mL) was added dropwise to a solution of 2-hydroxy-benzonitrile (47.6 g, 0.400 mmol) in CH3CN (500 mL) at 0° C., and then stirred at 0° C. for 20 min, then NIS (108 g, 0.48 mmol) was added. The reaction mixture was stirred at rt overnight, concentrated, then diluted with H2O (300 mL) and extracted with EA (300 mL×3). The combined organic parts were dried over anhydrous Na2SO4, filtered, and concentrated. Purification via FC (PE/EtOAc=5/1) afforded the title compound as a white solid (80 g).

Provenance & Evidence