2,6-Dibromopyridine → 6-Bromopyridine-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

Take up 2,6-dibromopyridine (0.500 g, 2.11 mmol) and CuCN (0.189 g, 2.11 mmol) in DMF (5.3 mL). Heat at 100° C. for 22 hours. Cool to room temperature. Add water (50 mL) and extract with ethyl acetate (3×100 mL). Wash the organic layer with brine (1×75 mL), dry over Na2SO4, filter and concentrate. Purify by flash chromatography, eluting with 15-40% ethyl acetate in hexanes to give the title compound (0.108 g, 30.0%): GC/MS, MS ES+ 182 (M−H)+, time 8.78 min, % of total 100%; TLC [silica gel 60 F254, 30% ethyl acetate in hexanes] Rf=0.29.

Provenance & Evidence