Dimethylformamide → 4-Chloro-2-(trifluoromethyl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

Add 4-chloro-1-iodo-2-trifluromethylbenzene (1500 mg, 4.89 mmol), zinc cyanide (345 mg, 2.94 mmol), and tetrakis(triphenylphosphine)palladium(0) (564 mg, 0.488 mmol) to anhydrous N,N-dimethylformamide (40 mL). Heat to 80° C. overnight. Cool to room temperature, dilute with toluene, wash with 2 N ammonium hydroxide (3×), saturated aqueous sodium chloride, dry, filter, concentrate to give a residue. Chromatograph the residue on silica gel eluting with hexanes/dichloromethane, to give 4-chloro-2-trifluoromethylbenzonitrile (630 mg, 63%): 1H NMR (400 MHz, CDCl3) δ 7.81-7.78 (m, 2H), 7.67 (dd, 1H, J=8.4, 2.4 Hz).

Provenance & Evidence