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

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.

Automated summary

Methyl 3-aryl-2-bromo-2-chloropropanoates were prepared via Meerwein reaction catalyzed by copper(II) bromide, and were utilized as starting materials for the synthesis of substituted 3-hydroxythiophenes. The structural variety of the obtained 2-substituted 5-aryl-3-hydroxythiophenes was achieved due to the wide range of available starting materials, including both anilines and thiols.