Bromoarylation of Methyl 2-Chloroacrylate under Meerwein Conditions for the Synthesis of Substituted 3-Hydroxythiophenes

Abstract

Methyl 3-aryl-2-bromo-2-chloropropanoates can be prepared by Meerwein reaction from methyl 2-chloroacrylate and various arenediazonium salts under copper(II) bromide catalysis. The resulting readily available compounds were used as starting materials in reactions with substituted methanethiols for the construction of substituted 3-hydroxythiophenes which have not yet been accessible by other routes. Structural variety of the obtained 2-substituted 5-aryl-3-hydroxythiophenes has been achieved due to a wide range of available starting materials, including both anilines and thiols.

Key words

Meerwein arylation - arenediazonium salts - 3-hydroxythiophenes - Fiesselmann reaction

Publication History

Received: 10 August 2021

Accepted after revision: 30 September 2021

Article published online:
05 November 2021

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