Silica gel-promoted convenient synthesis of 2-bromo-3-hydroxybenzoate derivatives |
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| Authors: | Hiroyuki Shinohara Motohiro Sonoda Naoya Hayagane Shota Kita Shinji Tanimori Akiya Ogawa |
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| Institution: | 1. Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuencho, Nakaku, Sakai, Osaka 599-8531, Japan;2. Department of Bioscience and Informatics, Graduate School of Life and Environmental Science, Osaka Prefecture University, 1-1 Gakuen-cho, Nakaku, Sakai, Osaka 599-8531, Japan |
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| Abstract: | A convenient silica gel-promoted synthesis of 2-bromo-3-hydroxybenzoate derivatives has been developed via the Diels–Alder reaction of furans with methyl 3-bromopropiolate, followed by a ring-opening aromatization. In addition, 2-bromo-3-methoxybenzoate, derived from 2-bromo-3-hydroxybenzoate with iodomethane, was found to be a good substrate for Pd-catalyzed cross-coupling reactions, despite its sterically hindered structure. |
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| Keywords: | Diels&ndash Alder reaction Ring-opening aromatization 2-Bromo-3-hydroxybenzoate Silica gel Furan |
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