Mechanistic study of silica-gel or FeCl3-promoted ring-opening aromatization of 7-oxanorborna-2,5-dienes affording 2-bromo-3-hydroxybenzoate derivatives
- Resource Type
- Original Paper
- Authors
- Sonoda, Motohiro; Ikeda, Ayu; Shinohara, Hiroyuki; Hayagane, Naoya; Ogawa, Akiya; Tanimori, Shinji
- Source
- Research on Chemical Intermediates. 45(1):13-21
- Subject
- One-pot reaction
Diels‒Alder reaction
Bromoalkyne
3-Hydroxybenzoate
Ring-opening aromatization
- Language
- English
- ISSN
- 0922-6168
1568-5675
One-pot synthesis of 2-bromo-3-hydroxybenzoates by the Diels–Alder reaction of furans with bromoalkyne and the subsequent ring-opening aromatization was studied by means of deuterium-labeling experiments. The residual protons in silica gel were considered to be the hydrogen source of the hydroxy group of products under the silica gel-promoted condition. The deuterium-labeling experiment revealed a rapid equilibrium among the intermediates prior to the aromatization under FeCl3-catalyzed condition.