Metal Template ortho-Acylation of Phenols. Direct Synthesis of Salicylic Acid Chlorides and Derivatives

Article abstract of DOI:10.1055/s-1988-27701

A direct synthesis of salicylic acid chlorides is achieved via "metal-driven" intracomplex acylation of bromomagnesium and aluminum phenoxides with phosgene.Salicylic acids 5 and some derivatives 6, 7 can be obtained by quenching the reaction mixture with convenient reagents.Moreover the reaction of lithium phenylacetylide with 3 provides a new convenient approach to ortho-hydroxyaryl alkynyl ketones like 8.The oriented complex 2, involving the metal phenoxide and phosgene is proposed to account for the ortho-regioselective control of the reaction.