Aminohaloborane in Organic Synthesis. X. A Convenient, Economical Exclusive ortho Substitution Reaction of N-Alkyl and N-Aminoalkyl Anilines

Abstract

A method for in situ generation of boron trichloride from boron trifluoride etherate and silicon tetrachloride in the presence of triethylamine, traced by boron-11 nuclear magnetic resonance (¹¹B-NMR) spectroscopy, was successfully developed, thus eliminating the need to use expensive boron trichloride for the exclusive ortho substitution reaction of N-monoalkylanilines. The method was readily adaptable to the reaction with N-monoaminoalkylanilines.