3,5-Dibromo-4-methylphenol (10.64 g, 40 mmol) and NaOH (2.08 g, 52 mmol) were suspended in water (50 mL), and dimethyl sulfate (4.6 mL, 48 mmol) was added slowly dropwise, with the dropwise acceleration rate being controlled to maintain the temperature of the reaction mixture below 35 °C. After dropwise addition, the reaction mixture was heated to reflux for 1.5 hours. After completion of the reaction, it was cooled to room temperature and extracted with EtOAc (3 x 50 mL). The organic phases were combined, washed sequentially with 2N NaOH solution (50 mL) and brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give a yellow solid. Purification by column chromatography (eluent: 10% EtOAc in heptane solution) afforded 2,6-dibromo-4-methoxytoluene as a white solid (9.35 g, 83% yield).1H NMR (300 MHz, CDCl3) δ 7.11 (s, 2H), 3.78 (s, 3H), 2.51 (s, 3H).
