Synthesis
General procedure for the synthesis of 4-chloro-7-iodoquinoline from 4-hydroxy-7-iodoquinoline: 4-hydroxy-7-iodoquinoline (4.5 g) was dissolved in 30 mL of phosphorus oxychloride (POCl3). The reaction mixture was heated to reflux for 2 hours. Upon completion of the reaction, the excess phosphorous trichloride was removed by distillation under reduced pressure. The residue was alkalized with ammonium hydroxide (NH4OH) to pH>7 and subsequently extracted with ethyl acetate (EtOAc). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 3.95 g (80% yield) of 4-chloro-7-iodoquinoline as a yellow solid.
References
[1] Patent: US2008/234267, 2008, A1. Location in patent: Page/Page column 13
[2] Patent: WO2005/63739, 2005, A1. Location in patent: Page/Page column 53
[3] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1980, vol. 16, # 7, p. 754 - 757
[4] Khimiya Geterotsiklicheskikh Soedinenii, 1980, # 7, p. 972 - 975
[5] Journal of the American Chemical Society, 1949, vol. 71, p. 3236
