Water → 5-Bromo-3-methylpyridine-2-carbonitrile

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A mixture of 2,5-dibromo-3-methylpyridine (20.17 g, 80.4 mmol) and copper(I) cyanide (7.24 g, 80.8 mmol) in 200 mL DMF was heated to 115° C. overnight. The reaction mixture was cooled to 25° C. and poured into 600 mL of H2O. The solid was filtered, washed with copious amounts of H2O. The filtrate was extracted with EtOAc (4×) and the combined organic layers were washed with H2O and dried over Na2SO4. The solution was filtered, evaporated onto silica gel and purified by flash chromatography eluting with EtOAc:hexane (0:1→1:9) to give the title compound as a white solid. MS m/z: 197.0 [M+1].

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