Synthesis
General procedure for the synthesis of 2-iodo-5-nitroanisole from 2-methoxy-4-nitroaniline: Potassium iodide (5.0 mmol) and sodium nitrite (3.0 mmol) were sequentially added to an acetic acid solution (30 mL) containing 2-methoxy-4-nitroaniline (2.5 mmol) and camphorsulphonic acid (3.0 mmol) at room temperature. The reaction mixture was stirred continuously for 24 h, during which nitrogen release was observed. Upon completion of the reaction, the reaction endpoint was confirmed by β-naphthol test and thin layer chromatography (TLC), followed by removal of solvent using a rotary evaporator. The resulting solid was washed with water and extracted with dichloromethane (CH2Cl2). The extract was dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure to remove the solvent. Finally, the product was purified by column chromatography, and the eluting solvent was a mixed system of hexane/dichloromethane. The physical properties and 1H NMR spectral data of the obtained product were consistent with the commercially available analytically pure sample.
References
[1] Tetrahedron, 2013, vol. 69, # 16, p. 3511 - 3517
[2] Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 10, p. 979 - 988
[3] Journal of Medicinal Chemistry, 2009, vol. 52, # 15, p. 4869 - 4882
[4] Chem. Zentralbl., 1901, vol. 72, # I, p. 739
[5] Privatmitteilung,
