Synthesis
GENERAL STEPS: To a dry round-bottomed flask fitted with a magnetic stirrer, a mixed solution of ethanol (75 mL) and ethyl acetate (30 mL) of 4-iodo-2-nitroanisole (16.2 g, 58 mmol) and tin(II) chloride dihydrate (65.5 g, 290 mmol) was added under nitrogen protection. The reaction mixture was heated and stirred at 70°C for 30 minutes. Subsequently, about half of the solvent was removed by evaporation and ether (100 mL) was added. The mixture was allowed to stand overnight in a refrigerator. The precipitate precipitated was collected by filtration and washed with ether. The resulting solid was dissolved in 15% aqueous sodium hydroxide solution (150 mL) and cooled in an ice bath. The mixture was extracted with dichloromethane, and the organic layer was sequentially washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 5-iodo-2-methoxyaniline (9.5 g, 38 mmol, 66% yield) as a white solid.
References
[1] Synlett, 2012, vol. 23, # 8, p. 1205 - 1208
[2] Synlett, 2013, vol. 24, # 14, p. 1772 - 1776
[3] Russian Chemical Bulletin, 2013, vol. 62, # 4, p. 1103 - 1110
[4] Izv. Akad. Nauk, Ser. Khim., 2013, # 4, p. 1102 - 1110,9
[5] Journal of the Chemical Society, 1916, vol. 109, p. 1087
