Ortho-Selective Nucleophilic Aromatic Substitution Reactions of Polyhaloanilines with Potassium/Sodium <i>O</i>-Ethyl Xanthate:  A Convenient Access to Halogenated 2(3<i>H</i>)-Benzothiazolethiones

Abstract

Polyhaloanilines bearing an ortho halogen atom undergo smooth nucleophilic aromatic substitution reactions with anionic sulfur nucleophiles at relatively mild temperatures (95−120 °C). These reactions are very efficient and highly ortho-selective. With potassium/sodium O-ethyl xanthate as a nucleophile, subsequent cyclization follows to afford halogenated 2(3H)-benzothiazolethiones (2-mercaptobenzothiazoles) in high yields