1-Bromo-2-Chloroethane → 1-(4-Bromophenyl)Cyclopropanecarbonitrile

Participants

Reaction Conditions

Reaction Steps

To a room temperature solution of 4-bromophenylacetonitrile (18.0 g) in a solution of 22 mL of sodium hydroxide (50% in water W/W) were added 1-bromo-2-chloroethane and (2.0 mL) and benzyltriethylammonium chloride (627 mg). The mixture was heated at 60° C. overnight. The reaction mixture was cooled to room temperature and diethyl ether was added (300 mL) and partitioned. The ether layer was washed with water (100 mL), hydrogen chloride (100 mL, 10% HCl in water) and brine. Then dried with magnesium sulfate and the solvent removed in vacuo. The residue was purified by swish using diethyl ether and hexanes to yield the title compound.

Provenance & Evidence