Bromine → 4-(Bromoacetyl)benzonitrile

Participants

Reaction Steps

To a mixture of para-cyanoacetophenone (52 g, 0.36 mol) in chloroform (520 ml) and 48% HBr (5.2 ml), a solution of bromine (19.3 ml) in chloroform (52 ml) was added dropwise over a period of 20 min. The mixture was stirred for 3 h at room temperature and neutralized to pH7 with sat. NaHCO3. The organic layer was washed with sat. NaCl and dried over anhydrous Na2SO4 and concentrated. The residue was chromatographed on silica gel (AcOEt/n-hexane=1/3 as an eluent) and recrystallized to obtain 2-bromo-4′-cyanoacetophenone as a colourless plate (23.4 g, 29%).

Provenance & Evidence