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GENERAL PROCEDURE: To a stirred solution of 4-chloro-2-iodobenzoic acid (1.0 eq.) dissolved in anhydrous methanol (2.0 mL/1.0 mmol of 4-chloro-2-iodobenzoic acid) was added sulfinyl chloride (2.0 eq.) dropwise at 0 °C. After addition, the reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the crude product was concentrated under reduced pressure, quenched with water and extracted with ethyl acetate. The organic layers were combined, washed with saturated aqueous sodium bicarbonate, dried over anhydrous sodium sulfate, concentrated by rotary evaporation, and finally purified by column chromatography to afford the target product methyl 4-chloro-2-iodobenzoate.

[1] Antimicrobial Agents and Chemotherapy, 2016, vol. 60, # 7, p. 3980 - 3987
[2] Patent: US2015/105351, 2015, A1. Location in patent: Paragraph 0451
[3] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 11, p. 1259 - 1262