2-(2-bromopyridin-3-yl)acetonitrile

5697-44-9

128071-75-0

1211523-71-5

GENERAL STEPS: A 1,2-dimethoxyethane solution (20 mL) of p-toluenesulfonylacetonitrile (5.08 g, 26.02 mmol) was added slowly and dropwise to a suspension of potassium tert-butoxide (t-BuOK, 5.92 g, 52.76 mmol) in 1,2-dimethoxyethane (50 mL) at -60 °C. Maintaining the temperature at -60 °C, a 1,2-dimethoxyethane solution (20 mL) of 2-bromo-3-pyridinecarboxaldehyde (4.81 g, 25.86 mmol) was added dropwise to the above reaction mixture. After the reaction mixture was stirred at -60 °C for 1 h, methanol (MeOH, 50 mL) was added, followed by slow warming of the reaction system to room temperature and continued stirring for 1 h. The reaction mixture was then heated to room temperature and stirring was continued for 1 h. The reaction mixture was then heated to a temperature of 0.5 °C. Next, the reaction mixture was heated to 85 °C and kept for 1 hour. After completion of the reaction, it was cooled to room temperature and the volatile solvent was removed under reduced pressure. The residue was diluted with saturated brine (200 mL) and extracted with ethyl acetate (EA, 3 x 150 mL). The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with the eluent of ethyl acetate:hexane (1:10, v/v) to afford the target product 2-(2-bromopyridin-3-yl)acetonitrile (2.21 g). Mass spectrometry (MS) analysis showed m/z 197 ([M+H]+).