1,2-Dibromoethane → 1-(3-Methoxyphenyl)cyclopropane-1-carbonitrile

Participants

Reaction Steps

To a stirred solution of 2-(3-methoxyphenyl)acetonitrile (6.5 g, 44.1 mmol), 40% aq tetrabutylammonium hydroxide (4.5 ml) and 50% aq NaOH (30 ml) in toluene (30 ml) was added 1,2-dibromoethane (10 ml, 116 mmol) at room temperature. The reaction mixture was stirred for 16 hours, diluted with EtOAc and washed with water and brine. The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a short silica gel column (hex:ethyl acetate, 9:1) to give the title compound.

Provenance & Evidence