Regioselective Preparation of Benzo[b]furans from Phenols and alpha-Bromoketones.

Regioselective Preparation of Benzo[b]furans from Phenols and alpha-Bromoketones. Journal of Organic Chemistry. 2012, vol 77, pp 266-275.

http://pubs.acs.org/doi/abs/10.1021/jo201841y

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.