1. Suspend p-bromomethylbenzoic acid (8.00 g, 37.2 mmol) in carbon tetrachloride (80 mL) under nitrogen protection with stirring. Sulfoxide chloride (6.8 mL, 93 mmol) was added slowly.
2. The reaction mixture was heated to reflux for 95 hours. Upon completion of the reaction, the reaction mixture was concentrated by rotary evaporator under reduced pressure to remove solvent and unreacted sulfoxide chloride.
3. The concentrated residue was dissolved in dichloromethane (150 mL) and ammonia (NH3) was passed through for 10 minutes and a yellowish precipitate was observed to form.
4. 5% aqueous sodium bicarbonate solution (70 mL) was added to the reaction mixture with vigorous stirring and the precipitate was collected by filtration.
5. The precipitate was washed with deionized water and subsequently dried under reduced pressure at 60 °C to afford 4-(bromomethyl)benzamide as a colorless solid (7.35 g, 92% yield).
