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Updated: May 27, 2026

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Regioselective preparation of benzo[b]furans from phenols and α-bromoketones
Leire Arias1, Yosu Vara, Fernando P Cossío
1Departamento de Química Orgánica I, Kimika Organikoa I Saila, Universidad del País Vasco, Euskal Herriko Unibertsitatea (UPV/EHU), Manuel de Lardizabal Etorbidea 3, 20018 San Sebastián, Donostia, Spain.
Abstract:
In this paper, a fully regiocontrolled synthesis of either 2- and 3-substituted benzo[b]furans is described. Direct reaction between phenols and α-bromoacetophenones in the presence of neutral alumina yields 2-substituted benzo[b]furans with complete regiocontrol. When a basic salt such as potassium carbonate is used, the corresponding 2-oxoether is obtained. Cyclization of these latter compounds promoted by neutral alumina yields the corresponding 3-substituted benzo[b]furans. Using the former method, Moracin M and other analogues can be obtained from commercial sources in two preparative steps. DFT calculations provide reasonable reaction paths to understand the formation of 2-substituted benzo[b]furans.
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