Improved Synthesis of the Benzyne Precursor 2-(Trimethylsilyl)phenyl Trifluoromethanesulfonate

An alternate procedure for the preparation of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate, a coveted benzyne precursor, is described. Modifications to existing methods result in a dramatic reduction in the overall reaction time and eliminate the use of organolithium reagents. This new procedure proceeds in four steps in 81% overall yield from 2-chlorophenol.