2-Bromo-4-methoxy-5-(benzyloxy)benzaldehyde

2973-59-3

100-39-0

6451-86-1

Under nitrogen protection, 2-bromo-5-hydroxy-4-methoxybenzaldehyde (8.70 mmol) was dissolved in 87 mL (0.1 M) of N,N-dimethylformamide (DMF) and cooled to 0 °C. Potassium carbonate (13.1 mmol, 1.8 g) and benzyl bromide (10.4 mmol, 1.77 g) were then added sequentially. The reaction mixture was slowly warmed to 25 °C and the reaction was stirred at this temperature for 5 hours. Upon completion of the reaction, the mixture was poured into 100 mL of aqueous ammonium chloride solution to quench the reaction. The reaction mixture was extracted with ethyl acetate (3 x 30 mL) and the organic layers were combined. The organic layer was washed with saturated saline (10 mL × 2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to afford 2-bromo-4-methoxy-5-benzyloxybenzaldehyde (5-(benzyloxy)-2-bromo-4-methoxybenzaldehyde) 2.73 g (8.53 mmol, 98% yield).