1-Bromo-2-Chloroethane → 1-(6-Chloropyridin-3-yl)cyclopropane-1-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a room temperature solution of (6-chloropyridin-3-yl)acetonitrile from Step 2 (6.1 g) in a solution of 9.9 mL of sodium hydroxide (50% in water W/W) were added 1-bromo-2-chloroethane (5.3 mL) and benzyltriethylammonium chloride (273 mg). The mixture was heated at 60° C. overnight. The reaction mixture was cooled to room temperature, poured into water (100 mL) and extracted with ethyl acetate (200 mL). The extracts were washed with saturated aqueous ammonium chloride 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