Efficient Procedure for the Preparation of 2-Bromofuran and Its Application in the Synthesis of 2-Arylfurans

Abstract

A simple, straightforward, and scalable procedure for the preparation of 2-bromofuran using N-bromosuccinimide (NBS) in dimethylformamide (DMF) is reported. The described preparation is conducted on a 20 to 50 g scale and does not require extractive workup procedures or chromatographic purifications. To illustrate the synthetic applications of 2-bromofuran, palladium-catalyzed Suzuki coupling reactions of the prepared 2-bromofuran with various aryl boronic acids were investigated, and moderate to good yields of 2-arylfurans were obtained.

Keywords:

• Bromination
• 2-bromofuran
• N-bromosuccinimide
• steam distillation
• Suzuki coupling

ACKNOWLEDGMENTS

This work was supported by Merck Frosst Centre for Therapeutic Research, Natural Sciences and Engineering Research Council of Canada (NSERC), and Boehringer Ingelheim (Canada) Ltd.

Notes

^a Isolated yield after column chromatography.