2-Aryloxy-2-methylpropionamides

Aryloxy-2-methylpropionamides 36 (Scheme 15) imderwent the rearrangement in anhydrous dioxane or, faster, in DMF in the presence of sodium hydride [28]. An important observation was made the presence... 

A one-pot procedure was developed for the preparation of aromatic amines from phenols via a one-pot Smiles rearrangement by N.P. Peet et al.° This new approach can be considered as an alternative of the Bucherer reaction which only works well for naphthalene derivatives and gives very poor yields for substituted benzene derivatives. In the current procedure, the phenol was reacted with 2-bromo-2-methylpropionamide to give 2-aryloxy-2-methylpropionamide which upon treatment with base underwent the Smiles rearrangement. The hydrolysis of the resulting A/-aryl-2-hydroxypropionamide afforded the aromatic amine. 

---