Elemental fluorine. Part 4. Use of elemental fluorine for the halogenation of aromatics

Abstract

New methodolgy for direct iodination of benzenoid compounds has been developed; the aromatic substrate is simply mixed with iodine and sulfuric acid, suspended in an inert medium, such as 1,1,2-trichlorotrifluoroethane (CF2CICFCl2) or perfluorocarbon, and elemental fluorine is passed through the system at room temperature. High conversions to iodoaromatic products occur, even with some deactivated systems, e.g. nitrobenzene. A very powerful brominating system is produced using the analagous methodology.