Tetrahedron

A new method for bromination of carbazoles, β-carbolines and iminodibenzyls by use of N-bromosuccinimide and silica gel

K Smith, DM James, AG Mistry, MR Bye, DJ Faulkner

Index: Smith, Keith; Martin James; Mistry, Anil G.; Bye, Martin R.; John Faulkner Tetrahedron, 1992 , vol. 48, # 36 p. 7479 - 7488

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Citation Number: 126

Abstract

Carbazole, N-ethylcarbazole, iminodibenzyl (10, 11-dihydro-5H-dibenz [b, f] azepine), N- ethyliminodibenzyl and imipramine are readily mono-, di-or polybrominated in high yields at ambient temperature in dichloromethane by use of the appropriate quantity of N- bromosuccinimide in the presence of silica gel. By contrast, the brominations of the β- carbolines, harmane and norharman, are less selective and give mixtures of products, ...