Synthesis
General procedure for the synthesis of 4-iodo-2-cresol from o-cresol: to a stirred solution of o-cresol (1 mmol) in dichloromethane (CH2Cl2) or 1,2-dichloroethane ((CH2Cl)2) (0.1 M) was sequentially added Ph3PAuNTf2 (0.025 mmol, 19 mg; if using a 2:1 Ph3PAuNTf2 with toluene complex with toluene) and N-iodosuccinimide (NIS, 1.1 mmol, 248 mg). The reaction mixture was stirred at room temperature or reacted under reflux conditions until complete conversion of o-cresol was confirmed by thin layer chromatography (TLC) monitoring. Upon completion of the reaction, the solvent was evaporated under reduced pressure and the resulting crude product was purified by fast column chromatography using different ratios of hexane and ethyl acetate (EtOAc) as eluents, resulting in pure 4-iodo-2-cresol.
References
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