Benzoic acid, 2-amino-4-chloro-5-iodo-, methyl ester

5900-58-3

199850-56-1

General procedure for the synthesis of methyl 4-chloro-5-iodo-2-aminobenzoate from methyl 2-amino-4-chlorobenzoate: Methyl 2-amino-4-chlorobenzoate (50 g, 0.27 mol) was added to a solution of anhydrous ethanol (2.5 L) containing iodine (68 g, 0.27 mol) and silver sulfate (84 g, 0.27 mol). The reaction mixture was stirred at room temperature for 45 minutes. Subsequently, the reaction mixture was filtered through a Celite pad to remove insoluble impurities. The filtrate was concentrated under reduced pressure and the residue was dissolved in ethyl acetate (2 L) and washed sequentially with saturated aqueous sodium bicarbonate (3 x 400 mL), water (3 x 400 mL) and brine. The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the target product methyl 2-amino-4-chloro-5-iodobenzoate (85 g, 99% yield).