1219741-79-3

The general procedure for the synthesis of 4-bromo-5-fluoro-2-iodoaniline from 4-bromo-3-fluoroaniline was as follows: N-iodosuccinimide (2.90 mL, 28.9 mmol) was slowly added to a solution of 4-bromo-3-fluoroaniline (5.00 g, 26.3 mmol) in acetic acid (52.6 mL). The reaction mixture was stirred at room temperature for 1.5 hours. Upon completion of the reaction, the reaction solution was diluted with toluene (20 mL) and subsequently concentrated under reduced pressure. The concentrated residue was dissolved in ethyl acetate and washed with 2N aqueous sodium hydroxide. The organic phase was further washed with saturated saline, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (using a 40-g Ultra SNAP column and a 25-g silica gel upconversion column with 2-10% ethyl acetate/heptane as eluent) to afford the target compound 4-bromo-5-fluoro-2-iodoaniline (7.23 g, 22.89 mmol, 87% yield). The product was confirmed by 1H NMR (400 MHz, chloroform-d): δ 7.74-7.78 (m, 1H), 6.53-6.57 (m, 1H). The mass spectrum (ESI) showed a m/z of 315.9 ([M + H]+).

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