Synthesis
The general procedure for the synthesis of 2-chloro-4-iodophenol from 4-iodophenol was as follows: 4-iodophenol, toluene and diisobutylamine were added to a round-bottomed flask under argon protection and heated up to 70 °C. SO2Cl2 was slowly added dropwise and the reaction mixture was kept stirred at 70°C for 1 hour. After completion of the reaction, the mixture was cooled, diluted with ether and washed once each with saturated aqueous NaHCO3 solution, saturated aqueous NaCl solution and H2O in turn. The organic phase was dried over MgSO4 and concentrated under reduced pressure to remove the solvent. The crude product was dissolved in a hexane:ether (4:1, v/v) solvent mixture and purified by silica gel column chromatography, using the same ratio of solvent system for elution. The final product was obtained as 2-chloro-4-iodophenol as a white solid in 90% yield.
References
[1] ACS Catalysis, 2018, vol. 8, # 5, p. 4033 - 4043
[2] Organic Letters, 2006, vol. 8, # 19, p. 4251 - 4254
[3] Patent: WO2010/59943, 2010, A2. Location in patent: Page/Page column 77; 78
[4] Organic Letters, 2018, vol. 20, # 23, p. 7726 - 7730
[5] Journal of the Chemical Society, 1912, vol. 101, p. 973
