New method for selective functionalization of fluoro- or ethylbenzene in the ortho position.

Abstract

A new o-functionalization of PhR (R = F, Et) is reported, involving a 2,5-disilylation with Me3SiCl in THF contg. Li. After aromatization, electrophilic substitution of the Me3Si group in position 2 and desilylation in position 5 gave 2,3-R1C6H3R (R = Ac, Bz, Br, iodo) are obtained in good yields. [on SciFinder(R)]