Acetonitrile → 5-Bromo-6-methylpyridine-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

3-Bromo-6-iodo-2-methylpyridine (1 equiv) and acetonitrile were combined and copper cyanide (0.5 equiv), sodium cyanide (0.8 equiv) were added. The reaction slurry was heated to 80° C. for 24 h. The reaction solution was cooled to room temperature and diluted with ammonium hydroxide (0.5 M aqueous solution). The mixture was stirred 15-30 min, filtered through diatomaceous earth and the filter cake was washed with ethyl acetate. The filtrate and wash were combined and diluted with ethyl acetate. The aqueous and organic phases were separated and the organic layer was washed with ammonium hydroxide (0.5 M aqueous solution) and saturated aqueous sodium chloride, dried, filtered, and concentrated under reduced pressure to provide 5-bromo-6-methylpicolinonitrile as a. MS (ESI) m/z 196.9 [M]+, 198.9 [M+2]+.

Provenance & Evidence