Thionyl Chloride → 3-(Chloromethyl)-4,5-difluorobenzenamine

Participants

Reaction Steps

To a stirring solution of (5-amino-2,3-difluorophenyl)methanol (4.13 g; 25.9 mmol) in DCM (78 mL) and NMP (11 mL) at RT was added dropwise thionylchloride (4.7 mL; 64.9 mmol). The mixture was allowed to react at RT overnight. Then, the mixture was poured into aqueous sodium bicarbonate solution/saturated aqueous sodium chloride solution/ice. The batch was stirred for 2 hours before it was extracted with ethyl acetate (2×). The combined organic phases were filtered using a Whatman filter and concentrated to give crude 3-(chloromethyl)-4,5-difluoroaniline.

Provenance & Evidence