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 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 layers are combined and washed with brine, dried over Na2SO4, filtered and concentrated. The product is purified by column to afford 626 mg 1-(5-bromo-pyridin-3-yl)-cyclopropanecarbonitrile (55% yield).

Provenance & Evidence