[Synthesis]
General procedure for the synthesis of 4-bromo-2-(bromomethyl)-1-methoxybenzene from 5-bromo-2-methoxybenzyl alcohol: (5-bromo-2-methoxyphenyl)methanol (1.0 g, 4.6 mmol) was dissolved in dichloromethane (10 mL) at 0 °C and tribromophosphine (1 M solution in dichloromethane, 9.2 mL, 9.2 mmol) was slowly added. After removing the ice bath, the reaction mixture was stirred at room temperature for 15 minutes. After completion of the reaction, the reaction solution was concentrated under reduced pressure and the residue was poured into cold saturated sodium bicarbonate solution and the organic phase was extracted with pentane. The organic phase was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford 4-bromo-2-(bromomethyl)-1-methoxybenzene (1.15 g, 89% yield) as a white crystalline solid. The product was characterized by 1H NMR (500 MHz, CDCl3) and 13C NMR (126 MHz, CDCl3) with the following data: 1H NMR δ 7.44 (d, J = 2.5 Hz, 1H), 7.38 (dd, J = 8.9, 6.1 Hz, 1H), 4.47 (s, 2H), 3.87 (s, 3H); 13C NMR δ 156.7, 133.6, 132.8, 128.4, 112.8, 112.7, 56.0, 27.5. |