Application of the anionic homologous Fries‐rearrangement to the synthesis of 3‐alkylbenzofuran‐2(3H)‐ones

Abstract

We have developed an effective organometallic-based procedure allowing the employment of 2-methylphenols as easily available starting materials in the synthesis of 3-alkylbenzofuran-2(3H)-ones. The first step of this protocol, an anionic homologous Fries-rearrangement, afforded 2-(2-tert-butyldimethylsilyloxyaryl)acetamides, which were selectively metalated and monoalkylated at the benzylic position. Acidic work-up of crude products afforded the desired heterocycles in satisfactory overall yields.