19056-41-8

3-Bromo-4-methoxyaniline is an intermediate used to prepare triazole analogs of combretastatin A-4 as cytotoxic agents and inhibitors of tubulin. It is also used in the synthesis of (1,2,4-oxadiazolyl)biphenylcarbonyltetrahydrospiro[furo]indolepiperidine (SB-224289) as selective 5-HT1B receptor inverse agonist.

General procedure for the synthesis of 3-bromo-4-methoxyaniline from 2-bromo-4-nitroanisole: 2-bromo-4-nitroanisole (0.1 g, 0.43 mmol) was suspended in unstabilized 57% hydriodic acid (1.3 mL), and the reaction was heated for 5 hr at 90 °C. After completion of the reaction, the reaction mixture was cooled, diluted with ethyl acetate (5 mL) and washed sequentially with saturated aqueous sodium thiosulfate and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The crude product was further purified by silica gel column chromatography to afford 3-bromo-4-methoxyaniline (0.07 g, 80% yield).

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