Synthesis of Alkyl 2-Bromomethyl-4-(diethoxyphosphorylmethyl)-5-tert-butylfuran-3-carboxylates and Their Reactions with Nucleophilic Agents

Abstract

Alkyl 2-methyl-4-(diethoxyphosphorylmethyl)-5-tert-butylfuran-3-carboxylates are selectivelybrominated with N-bromosuccinimide at the methyl group in position 2 of the ring. The resulting bromo-methyl derivatives react with secondary amines to form tertiary amines, with sodium butylthiolate inmethanol to form the corresponding sulfide. The reaction with potassium thiocyanate in DMF at 80°C givesa mixture of thiocyanate and isothiocyanate. When treated with phenolate or alcoholate ions, the bromomethylfurans decompose.