Metalation Reactions of 3,5-Dichloro-N,N-diethylbenzamide

Abstract

The competing influences of regiocontrol of the diethylamido and chloro functional groups were examined in the metalation reactions of 3,5-dichloro-N,N-diethylbenzamide. The compounds, 3,5-dichloro-4-methyl-N,Ndiethylbenzamide and 2,6-dichloro-4-N,Ndiethylamide benzoic acid, were synthesized by reacting 3,5 -dichloro-N,N -diethy lbenzamide with butyllithium (BuLi) followed by iodomethane (CH3I) and carbon dioxide (C02), respectively. The observed site of metalation was controlled by the chlorine substituents, rather than the amide substituent. The products were characterized using silicagel TLC, Varian Gemini 300MHz 1H-NMR spectroscopy, and mass spectroscopy (MS).