1-Bromo-2-Chloroethane → 1-(6-Chloropyridin-3-yl)cyclopropane-1-carbonitrile

Participants

Reaction Steps

To a stirred mixture of the (6-chloropyridin-3-yl)acetonitrile (8.00 g, 0.0524 mol), benzyltriethylammonium chloride (0.8 g, 0.004 mol), and 1-bromo-2-chloro-ethane (8.69 mL, 0.105 mol) was added dropwise sodium hydroxide, 50% aqueous solution (16.1 mL, 0.419 mol) at 50° C. After stirring for 2 h, the reaction mixture was diluted with water and the resulting layers were separated. The aqeous layer was extracted with dichloromethane. The combined organic layers were washed with 1N HCl and brine succesively, dried with magnesium sulfate, filtered, and concentrated in-vacuo. The crude product was purified by combiflash to obtain 2.5 g of pure product as a white solid.

Provenance & Evidence