6-Bromomethyl-nicotinonitrile

3222-48-8

158626-15-4

Example 50 General procedure for the preparation of 6-bromomethylnicotinonitrile (11-2): to a solution of 6-methylnicotinonitrile (11-1) (15 g, 127 mmol) in carbon tetrachloride (300 mL) was added N-bromosuccinimide (27.12 g, 152.4 mmol). The reaction mixture was degassed and displaced three times with nitrogen, followed by the addition of AIBN (2,2'-azobisisobutyronitrile) (2.08 g, 12.6 mmol). After stirring the reaction at 85 °C for 7 h, AIBN (1.04 g) was added and the reaction was continued for 1 h. The reaction was completed with the addition of AIBN (2,2'-Azobisisobutyronitrile). After completion of the reaction, the solvent was removed by distillation under reduced pressure. The crude product was purified by silica gel column chromatography with the eluent being a mixed solvent of ethyl acetate/hexane to give 10 g of the target product 6-bromomethylnicotinonitrile in 40% yield.