Potassium Cyanide → (4-Bromo-2-chlorophenyl)acetonitrile

Participants

Reaction Steps

To a magnetically stirring solution of 4-Bromo-1-bromomethyl-2-chloro-benzene (3.59 g, 12.67 mmol) from step 2 below and tetrabutylammonium bromide (0.41 g, 1.27 mmol) in CH2Cl2/H2O 1:1 (60.0 mL), was added a solution of KCN (2.48 g, 38.01 mmol) in H2O (30 mL). The resulting orange mixture was stirred at room temperature for 3 hours. The layers of the resulting reaction mixture were separated and the organic layer was washed with NaHCO3 sat solution (3×50 mL), then dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (30% EtOAc in Hexanes) to yield the intermediate as a clear oil (3.59 g, 100%). 1H NMR (400 MHz, CDCl3): δ 3.79 (s, 2H), 7.37–7.60 (m, 3H).

Provenance & Evidence