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

Participants

Reaction Steps

A solution of the compound (22.6 g, 23.36 mmol) obtained in Example 14-1), 1-bromo-2-chloroethane (18.9 g, 132 mmol), benzyltriethylammonium chloride (0.48 g, 2.34 mmol), and potassium hydroxide (41.5 g, 739 mmol) in water (40 mL) was stirred at 40° C. for 9 h. The reaction mixture was cooled to room temperature and extracted with ethyl acetate, and the organic layer was washed with water, a 1 M aqueous hydrochloric acid solution, and saturated sodium chloride solution and dried with anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by silica gel column chromatography (Isco Combiflash, 40 g, hexane:ethyl acetate=0:100 to 100:0, gradient) to obtain the title compound (24.6 g, 97%) as a black oily substance.

Provenance & Evidence