1,2-Dibromoethane → 1-(4-Bromo-3-fluorophenyl)cyclopropane-1-carbonitrile

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Reaction Steps

A solution of 4-bromo-3-fluorophenylacetonitrile (1 g, 4.6 mmoles) in toluene (4 ml) is mixed with 0.6 ml (7 mmoles) of 1,2-dibromoethane, a 50% NaOH aqueous solution (4 ml), and tetrabutylammonium bromide (0.32 g, 1 mmoles). The mixture is kept under stirring at room temperature for 4 hours, then diluted with water and extracted with ethyl acetate. The organic phase is recovered, and the solvent is eliminated under vacuum to give a brown solid, which is subjected to silica gel chromatography purification, to afford an orange to yellow product in the solid form (1 g, yield 90%).

Provenance & Evidence