Hydrochloric Acid → 1-(4-Bromophenyl)cyclopropane-1-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 4-bromophenylacetonitrile (50.0 g, 255 mmol), 1-bromo-2-chloroethane (26.5 mL, 319 mmol), benzyltriethylammonium chloride (1.16 g, 5.10 mol), and potassium hydroxide (100 g, 1.79 mol) in water (100 mL) was stirred at 50° C. for 3 h. Ethanol (400 mL) was added to the reaction mixture, and the mixture was stirred at 100° C. for 3 days. The reaction mixture was neutralized by pouring it into 5 N hydrochloric acid (360 mL) with ice cooling. The reaction mixture was extracted with dichloromethane, the organic layer was dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. Diisopropyl ether was added to the residue, and the precipitate was collected by filtration and dried under reduced pressure to obtain the title compound (50.4 g, 82%) as a white solid.

Provenance & Evidence