Methanol → Methyl 2-bromo-5-methoxybenzoate

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To a solution of 2-bromo-5-methoxybenzoic acid (150 g, 649 mmol) in Methanol (1500 mL) stirred under nitrogen at 0° C. was added sulfurous dichloride (69.4 mL, 974 mmol) dropwise during 30 min. The reaction mixture was stirred at 65° C. for 12 hr. The solvents were evaporated off, then water (750 mL) and EtOAc (750 mL) was poured into the residue. The mixture was partitiononed. The aqueous layer was extracted with EtOAc (250 mL*3). Combined organic phase was washed with water (200 mL*2), dried over anhydrous Na2SO4 and concentrated to give 150 g (90%) of the title compound.

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