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

L Gavara, T Boisse, B Rigo, JP Henichart

Index: Gavara, Laurent; Boisse, Thomas; Rigo, Benoit; Henichart, Jean-Pierre Tetrahedron, 2008 , vol. 64, # 22 p. 4999 - 5004

Full Text: HTML

Citation Number: 24

Abstract

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 HCl instead of HBr, chlorination can also be performed in few cases. The i-amONO2/HBr mixture can also be utilized for bromination in the α-position of electron withdrawing groups. A possible mechanism is briefly discussed.