1-Bromo-2-Chloroethane → 1-(4-Bromo-3-fluorophenyl)cyclopropane-1-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a room temperature solution of (4-bromo-3-fluorophenyl)acetonitrile from Step 3 (6.4 g) in a solution of 7.5 mL of sodium hydroxide (50% in water W/W) were added 1-bromo-2-chloroethane (4.0 mL) and benzyltriethylammonium chloride (204 mg). The mixture was heated at 60° C. for 5 hours. The reaction mixture was cooled to room temperature and poured into water (100 mL). Extracted with ethyl acetate (200 mL). The extracts were 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 methyl t-butyl ether and hexanes to yield the title compound.

Provenance & Evidence