Organic process research and development p. 861 - 866 (2020)
Update date:2022-08-04
Topics:
Aronow, Jonas
Chassagne, Pierre
Cortes-Clerget, Margery
Erb, Bernhard
Gallou, Fabrice
Gallou, Isabelle
Jager, Andreas
Marti, Michael
Nuzzo, Gian-Luca
Seeger, Manuela
Benzofuran scaffolds are fundamental moieties found in a variety of biologically active natural products and synthetic drugs. In the course of one of our development programs, we needed to develop a practical and cost-effective manufacturing approach to such a benzofuran scaffold. Here we report a highly robust four-step, one-pot process that provides access to a 6-hydroxybenzofuran-3-carboxylic acid structure. An 1H NMR monitoring study allowed a better understanding of the overall sequence of events and the nature of the detected intermediates. After six steps, including the optimized tandem process, the desired hydroxylated benzofuran was obtained in 40% yield with a purity above 99%.
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