[Synthesis]
N-(2-methoxybenzyl)acetamide (6.5 g, 0.036 mol) was used as starting material and dissolved in dichloromethane (DCM, 100 mL). The solution was cooled to -10 °C under nitrogen protection. Subsequently, boron tribromide (BBr3, 15 mL, 0.15 mol) was slowly added dropwise. After the dropwise addition was completed, the ice bath was removed and the reaction mixture was allowed to react at room temperature with stirring for 2 hours. Upon completion of the reaction, the mixture was again cooled to -10 °C and water (20 mL) was slowly added to quench the reaction. The reaction mixture was extracted with dichloromethane (3 x 100 mL), the organic layers were combined, washed sequentially with water (3 x 100 mL) and brine (100 mL), and dried to give N-(2-hydroxybenzyl)acetamide (4.3 g, 71.7% yield) as a solid product. The product did not require further purification and could be used directly in the subsequent reaction. The product was characterized by 1H NMR (300 MHz, DMSO-d6) and LC-MS: 1H NMR δ 9.56 (brs, 1H), 8.27 (brs, 1H), 7.09-7.03 (m, 2H), 6.79-6.72 (m, 2H), 4.16 (d, J = 6.0 Hz, 2H), 1.87 (s, 3H); LC- MS m/z 166.2 [M + H]+, retention time tR = 1.15 min. |