Hydrochloric Acid → 2,4-Dibromobenzonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of copper(I) cyanide (2.32 g, 25.9 mmol) in anhydrous dimethylsulfoxide (50 mL) is stirred at 60° C., and to this solution is added tert-butylnitrite (7.1 mL, 59.7 mmol) all at once. A solution of 2,4-dibromoaniline (5.0 g, 19.9 mmol) in anhydrous dimethylsulfoxide (30 mL) is added dropwise, via cannula, to the mixture. After the addition is complete the reaction mixture is stirred for 1 hr, cooled to 45° C., and then treated slowly with 5N HCl (50 mL). Five minutes later, the reaction mixture is cooled to ambient temperature and extracted with 1:1 ethyl acetate:hexane (2×300 mL). The combined organic layers are washed with water (100 mL) and saturated aqueous sodium chloride (100 mL), dried, concentrated under reduced pressure and the residue subjected to silica gel chromatography, eluting with hexane containing from 0–5% ethyl acetate. Fractions containing product are combined and concentrated under reduced pressure to provide the title compound (1.61 g, 31% yield).

Provenance & Evidence