Acetonitrile → 2-(6-Bromopyridin-2-yl)acetonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of MeCN (14.29 mL, 274 mmol) in THF (300 mL) at −78° C. was added n-butyllithium (2.5 Min hexanes, 100 mL, 251 mmol). After stirring for 30 minutes at −78° C., 2,6-dibromopyridine (18.0 g, 76 mmol) in THF (100 mL) was added. The reaction was stirred at −78° C. for 45 minutes, warmed to room temperature over 45 minutes, and quenched with water. The mixture was extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried (MgSO4), and concentrated in vacuo. Flash chromatography (silica, 0-40% ethyl acetate/hexanes) afforded the title compound as a yellow solid. LRMS (APCI) calcd for C7H6BrN2 [M+H]+ 197, found 197.

Provenance & Evidence