A new method of bromination of aromatic rings by an iso-amyl nitrite/HBr system

摘要

A mixture of iso-amyl nitrite/HBr is shown to be a mild and efficient reagent for electrophilic aromatic bromination. The reaction succeeds with slightly activated arenes and heterocyclic compounds. By using FIG instead of HBr, chlorination can also be performed in few cases. The i-amONO(2)/HBr mixture can also be utilized for bromination in the alpha-position of electron withdrawing groups. A possible mechanism is briefly discussed. (C) 2008 Elsevier Ltd. All rights reserved.