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General procedure for the synthesis of methyl 5-chloro-2-iodobenzoate from methanol and 5-chloro-2-iodobenzoic acid: a mixture of 5-chloro-2-iodobenzoic acid (3.0 g, 10.62 mmol), dichlorosulfoxide (12 mL), and N,N-dimethylformamide (0.6 mL) was gently heated with a heat gun until a homogeneous solution was formed (about 15 minutes). Subsequently, the reaction solution was continued to be stirred at 23 °C for 30 min, after which the solvent was removed by concentration under reduced pressure. Methanol (24 mL) was added to the crude product and stirred at 23 °C for 30 min. After the reaction was completed, the reaction solution was again concentrated under reduced pressure. The crude product was purified by rapid chromatography on a Biotage silica gel column with a gradient of cyclohexane to cyclohexane:ethyl acetate (85:15) as eluent to give methyl 5-chloro-2-iodobenzoate (3.02 g, 10.20 mmol, 96% yield).UPLC-MS analysis showed a retention time of 1.17 min and a molecular ion peak m/z 296.6 [M + H]+ , analyzed by method 12.

[1] Patent: WO2015/91685, 2015, A1. Location in patent: Page/Page column 69
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 10, p. 2823 - 2827
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 28, p. 7177 - 7180