In solution, 4-Iodothioanisole shows a yellowish color due to intramolecular excitation of the cyclopentene system, while in the solid state it is orange because of free rotation around the carbon-iodine bond.It reacts with electrophiles to form carbon-iodine bonds and can be used to make cross-coupling reactions.
General procedure for the synthesis of 4-iodoanisole from 4-methylthiophenylboronic acid: KX (X = I, Br) (0.2 mmol), 4-methylthiophenylboronic acid (0.3 mmol), CuBr2 (4.5 mg, 10 mol%), 1,10-phenanthroline (7.2 mg, 20 mol%), and DMF ( 2 mL). The reaction mixture was stirred at 80 °C or 130 °C for the reaction. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the residue was purified by rapid column chromatography on silica gel to afford the target product 4-iodoanisole.
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