The Iodination of Aromatic Compounds. I. The Action of Iodine on Aniline in the Presence of Mercuric Oxide

Abstract

A satisfactory process for the preparation of p-iodo- and 2,4-diiodo-aniline has been developed, aniline being treated with iodine in the presence of mercuric oxide. Acetanilide was also iodinated by this procedure. When lead, calcium, and ferric oxides were employed the yields of p-iodo-aniline proved to be only slightly greater than that obtained by the action of iodine alone, whilst zinc oxide lowered the yield considerably. The influence of added iodides, acids, and mercuric iodide on the rate of reaction of iodine and aniline was investigated. A theory has been proposed to explain the role of mercuric oxide in effecting the iodination of aniline.