1,3-Dibromopropane → 1-(4-Bromophenyl)cyclobutanecarbonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of potassium hydroxide (56.5 g) and tetrabutylammonium bromide (2.92 g) in toluene (400 mL) and water (30 mL) was warmed to 70° C. Then, 1,3-dibromopropane (39.0 g) and 2-(4-bromophenyl)acetonitrile (35.5 g) were sequentially added thereto, and the mixture was stirred at 100° C. for 3 hours. After the reaction mixture was cooled to 80° C., heptane (100 mL) was added thereto, and the mixture was further cooled to room temperature. The reaction mixture was filtered and washed with hexane, and the organic layer was separated. The obtained organic layer was washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane:ethyl acetate) to give the desired product (24.0 g, yield: 56%) as a colorless oil.

Provenance & Evidence