General procedure for the synthesis of methyl 2-amino-5-bromo-3-iodobenzoate from methyl 5-bromoaminobenzoate: 371 mg of methyl 2-amino-5-bromobenzoate (2 mmol) was dissolved in 2 mL of concentrated acetic acid, and 495 mg of N-iodosuccinimide (2.2 mmol) was added and the reaction was carried out for 17 hours at room temperature. After completion of the reaction, the mixture was poured into a mixture of 5 mL of saturated sodium bicarbonate solution and ice and extracted twice with ethyl acetate (EtOAc). The organic phases were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 585 mg of methyl 2-amino-5-bromo-3-iodobenzoate (82% yield) as a light brown solid. Mass spectrometry (EI) showed a molecular ion peak m/z 354.9 (M+).
