Metalation Reaction of 3,5-Dichloro-N-ethylbenzamide

Abstract

The metalation reaction of 3,5-dichloro-Nethylbenzamide was compared with that of 3,5-dichloro-N,N-diethylbenzamide in order to study the effects of regioselectivity and sterics of the functional groups. This is a continuation of the research performed by Demas and Bradley, 1998. The substituted 3,5-dichloro-N-ethylbenzamide was synthesized by reacting the benzamide with a base, sec-butyllithium, followed by the addition of an electrophile, benzyl bromide. All the products were characterized by thin-layer chromatography (TLC), Varian Gemini 300MHz Proton Nuclear Magnetic Resonance (IHNMR), and Perkin Elmer 2000 Fourier Transform Infrared Spectrometer (IR).