Procedure for the synthesis of 1-bromo-4-(bromomethyl)-2-toluene: To a solution of 4-bromo-3-methylbenzyl alcohol (27.5 g, 136.8 mmol) in dichloromethane (250 mL) was added triphenylphosphine (39.4 g, 150.5 mmol) and carbon tetrabromide (49.9 g, 150.5 mmol) in sequence. The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, water was added to quench the reaction. The organic layer was separated and dried over anhydrous sodium sulfate, followed by concentration under reduced pressure to remove the solvent. The crude product was purified by column chromatography to afford 1-bromo-4-(bromomethyl)-2-toluene (34 g, 94% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 7.94-7.92 (d, 1H), 7.70 (s, 1H), 7.53-7.51 (d, 1H), 4.86 (s, 2H), 2.83 (s, 3H).
