General procedure for the synthesis of methyl 2-bromomethyl-5-methoxybenzoate from methyl 2-methyl-5-methoxybenzoate: Preparation of intermediate 12: Compound 11 (4.4 g, 24.2 mmol) was dissolved in carbon tetrachloride (80 mL) and N-bromosuccinimide (4.48 g, 24.2 mmol) and benzoyl peroxide (276 mg 1.13 mmol). The reaction mixture was heated to reflux and stirred for 3 hours. After completion of the reaction, the solid insoluble material was removed by filtration and the filter cake was washed with ether. The organic phases were combined, washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the target product 12 (6.1 g, 98% yield). Product characterization data: mass spectrum (LCMS) m/z 260 ([M+H]+), 1H NMR (CDCl3) δ 4.50 (2H, s, CH2Br), 3.73 (3H, s, OCH3), 3.88 (3H, s, CO2CH3), 6.86-7.50 (m, 3H, Ar-H).
