188813-07-2

188815-32-9

74-88-4

188813-07-2

(a) Synthesis of methyl 3-bromo-5-iodobenzoate: In a dry reaction flask, 3-bromo-5-iodobenzoic acid (15 g, 45.9 mmol) was dissolved in a solvent mixture of tetrahydrofuran (20 mL) and N,N-dimethylformamide (75 mL). Sodium carbonate (9.7 g, 92 mmol) and iodomethane (5.7 mL, 92 mmol) were then added. The reaction mixture was stirred at room temperature for 20 hours. After completion of the reaction, most of the solvent was removed by concentration under reduced pressure. The residue was extracted with ethyl acetate and washed sequentially with water, saturated aqueous sodium bicarbonate solution and brine. The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound methyl 3-bromo-5-iodobenzoate. Yield: 15 g (99% yield).