Tetramethylammonium Dichloroiodate

Experimental procedure¹⁾: The aromatic compound (5.0 mmol) is added to tetramethylammonium dichloroiodate (1.4 g, 5.0 mmol) in a mortar. The reaction mixture is ground with a pestle to produce a homogeneous powder, and the mixture is left for 5 ~ 45 min at room temperature. When TLC shows complete disappearance of starting aromatic compound, to the brown solid is added 5 mL of sodium bisulfate (5%) and the reaction mixture is extracted with ether (3 × 5 mL). The combined extracts are dried with MgSO₄. Evaporation of the solvent gives corresponding iodoaromatic derivatives. The product is purified by column chromatography on silica gel using a mixture of hexane/EtOAc (80:20).