Methanol → 2-(2-Bromo-4-chlorophenyl)-acetamidine hydrochloride

Participants

Reaction Steps

To a stirred suspension of NH4Cl (9.241 g, 169.565 mmol) in dry toluene (120 mL) was added tri-methyl aluminum (2M) (45.23 mL, 90.435 mmol) at 5° C. the reaction mixture was warmed to room temperature and the reaction mixture was stirred for 2 h. A solution of (2-bromo-4-chlorophenyl)-acetonitrile (374) (13 g, 56.522 mmol) in toluene (30 mL) was added to the above reaction mixture and the reaction mixture was stirred for 14 h at 80° C. while silica thin layer chromatography was performed (10% methanol in dichloromethane; Rf=0.2). After completion of the reaction, the reaction mixture was quenched with a suspension of silica gel (20 g) in chloroform (200 mL) and the reaction mixture was stirred for half an hour at room temperature and filtered. The silica gel was washed with methanol (100 mL) and the combined filtrate was concentrated under reduced pressure to get 2-(2-bromo-4-chlorophenyl)-acetamidine hydrochloride (375) (14.0 g, 87.68%) as a white solid.

Provenance & Evidence