Aromatic Iodination of Activated Arenes and Heterocycles with Lead Tetraacetate as the Oxidant

Abstract

An easy, cheap and fairly quick laboratory method is presented for aromatic iodination of some highly activated arenes and heterocycles with molecular iodine in the presence of either pure lead tetraacetate dissolved in glacial acetic acid, or with the same oxidant but prepared in situ from Pb₃O₄ dissolved in hot AcOH/Ac₂O prior to the iodination. 4-Bromo- and 2,4-dibromoanisoles are obtained from anisole by the respective oxidative bromination.