Step 2: To a solution of 2-bromo-3-methylbenzamide (12 g, 56.1 mmol) in N,N-dimethylformamide (DMF, 100 mL) was slowly added a solution of cyanuric chloride (15.47 g, 84.1 mmol) in DMF (50 mL) at 0 °C and under nitrogen protection. After addition, the reaction mixture was brought to room temperature and stirred overnight. Thin layer chromatography (TLC, unfolding agent: petroleum ether/ethyl acetate = 1:1) was monitored to show complete reaction. The reaction mixture was poured into water (500 mL) and extracted with ethyl acetate (EtOAc, 200 mL x 2). The organic phases were combined and washed sequentially with saturated aqueous sodium carbonate (200 mL × 2), saturated saline (200 mL × 4), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 2-bromo-3-methylbenzonitrile (11 g, 100% yield) as an off-white solid.1H NMR (400 MHz, CDCl3): δ 7.51-7.45 (m, 2H), 7.33 -7.29 (m, 1H), 2.47 (s, 3H).
