Example 9.1: Synthesis of 5-bromo-3-methylpyridine-2-carbonitrile.
To a solution of 2,5-dibromo-3-methylpyridine (2.5 g, 9.96 mmol) in dimethylformamide (10 mL) was added cuprous cyanide (892 mg, 9.96 mmol), and the reaction mixture was stirred for 12 hours at 120 °C. Upon completion of the reaction, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated. Purification by column chromatography gave a white solid product (970 mg, 57.6% yield).
Product characterization data: 1H NMR (300 MHz, CDCl3): δ 8.55 (s, 1H), 7.64 (t, 1H), 2.54 (s, 3H).
