1-Chloro-2-iodoethane is used as a mild electrophile for iodination of metallated species, as in the conversion of an ortho-lithiated benzyl ether to the corresponding ortho-iodide. It reacts with 5-hydroxy-[1,4]naphthoquinone, and obtain the 5-(2-chloro-ethoxy)-[1,4]naphthoquinone.