1,2-Dibromoethane → 1-(3-Chlorophenyl)cyclopropanecarbonitrile

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To a solution of 2-(3-chlorophenyl)acetonitrile (3.2 g, 21 mmol) and 1,2-dibromoethane (3 mL, 35 mmol) in toluene (20 ml), 35% sodium hydroxide and tetrabutylammonium iodide (400 mg, 1.3 mmol) were added. The mixture was vigorously stirred at room temperature for 4 hours. The resulting solution was diluted with water and extracted with ethyl acetate. The organic solution was concentrated to afford brown oil. Chromatography on silica gel (hexane/ethyl acetate=5/1) afforded 1-(3-chlorophenyl)cyclopropanecarbonitrile (2.1 g, 56% yield) as light yellow oil.

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