Toluene → 4-PHENYLAMINO-BENZONITRILE

Participants

Reaction Conditions

Reaction Steps

To a mixture of sodium tert-butoxide (7.44 g, 77.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.38 g, 0.415 mmol) and rac-2,2-bis(diphenylphosphino)-1,1-binaphthyl (0.172 g, 0.277 mmol) was added a solution of 4bromobenzonitrile (10 g, 55.3 mmol) and benzylamine (6.5 mL, 0.11 mol) in toluene (100 mL) under nitrogen atmosphere, and the solution was stirred at 80° C. for 5 hours. The reaction mixture was allowed to room temperature, then, filtered through Celite pad to remove insoluble matter, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate), and 4-phenylamino-benzonitrile (6.7 g, 63%) was obtained as a yellow solid.

Provenance & Evidence