Synthesis
General procedure for the synthesis of 4-iodo-3-nitroanisole from 2-nitro-4-methoxyaniline: 11.9 mmol of 2-nitro-4-methoxyaniline was dissolved in 20 mL of concentrated sulfuric acid at a mass concentration of 71%. The temperature of the system was lowered to -5°C. 10 mL of 2 mol/L sodium nitrite solution was rapidly added to the reaction system at 0 °C and under vigorous stirring. The reaction was kept at 0°C for 10 minutes. Subsequently, the reaction mixture was poured into 5 mL of 4 mol/L sodium iodide solution at 0 °C and the reaction was continued for 30 min. Upon completion of the reaction, the solid residue was collected by filtration and washed sequentially with 6N hydrochloric acid and water. The crude product was recrystallized by hexane to give a yellow solid A.
References
[1] Patent: CN105669525, 2016, A. Location in patent: Paragraph 0072; 0073; 0082
[2] Synlett, 2016, vol. 27, # 14, p. 2095 - 2100
[3] Synlett, 2005, # 16, p. 2469 - 2472
[4] Journal of Organic Chemistry, 2001, vol. 66, # 13, p. 4525 - 4542
[5] Angewandte Chemie - International Edition, 2011, vol. 50, # 32, p. 7354 - 7358
