Methanol → 2-(5-Bromopyridin-3-yl)acetonitrile

Participants

Reaction Conditions

Reaction Steps

To SOCl2 (26.7 ml) cooled with an ice-bath was added portionwise (5-bromo-pyridin-3-yl)-methanol (ABCR, Karlsruhe, Germany, 26.6 mmol). The RM was refluxed for 1 h then was cooled at 0° C. and quenched with diethyl ether. The resulting precipitate was filtered, washed with cooled diethyl ether and dried under vacuum at 50° C. The solid was mixed with potassium cyanide (64.5 mmol), MeOH (35 ml) and water (14 ml) and the RM was refluxed for 2 h. The RM was cooled, quenched with aqueous K2CO3 and extracted with diethyl ether (3×). The combined organic layers dried over Na2SO4, filtered and evaporated to give the title compound as a purple solid. (HPLC: tR 2.16 min (Method A); M+H=197, 199 MS-ES)

Provenance & Evidence