1-Bromo-2-Chloroethane → 1-(5-Bromopyridin-3-yl)cyclopropane-1-carbonitrile

Participants

Reaction Steps

To a suspension of (5-bromo-pyridin-3-yl)-acetonitrile (1.0 g, 5.1 mmol) in 50% NaOH (20.000 ml) is added 1-bromo-2-chloro-ethane (764 mg, 5.33 mmol) and benzyl triethylammonium chloride (15 mg, 0.11 mmol). The resultant mixture is heated to 60° C. for 2 h. After cooling down to room temperature, EtOAc is added and extracted. The organic layer is combined and washed with brine, dried over Na2SO4, filtered and concentrated. The product is purified by column to afford 626 mg of 1-(5-bromo-pyridin-3-yl)-cyclopropanecarbonitrile (55% yield).

Provenance & Evidence