2-IODO-4-METHOXYPHENYLAMINE

157496-75-8

191348-14-8

The general procedure for the synthesis of 2-iodo-4-methoxyaniline from tert-butyl (2-iodo-4-methoxyphenyl)carbamate was as follows: tert-butyl (2-iodo-4-methoxyphenyl)carbamate (3.5 g, 10.0 mmol) was slowly added to a solution of (2-iodo-4-methoxyphenyl)carbamate in dichloromethane (50 mL) at 0 °C with trifluoroacetic acid (8.9 mL, 120.0 mmol). The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the mixture was cooled to 0 °C and the reaction was quenched with 2N sodium hydroxide solution (95 mL), followed by adjusting the pH to 8 with 2N hydrochloric acid (70 mL).The organic and aqueous layers were separated, and the aqueous layer was extracted with dichloromethane (2 x 70 mL). All organic layers were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by fast column chromatography (silica gel, n-hexane/ethyl acetate = 7:1) to give 2-iodo-4-methoxyaniline (2.12 g, 85% yield) as an orange oil.