Steric Hindrance Effect Leading to Regioselective Bromination of Phenols with HBr
- Corresponding author: Ma Xiantao, xiantaoma@126.com
Citation:
Ma Xiantao, Zhou Kunjie, Ren Mengjuan, Wang Mengyu, Yu Jing. Steric Hindrance Effect Leading to Regioselective Bromination of Phenols with HBr[J]. Chinese Journal of Organic Chemistry,
;2019, 39(10): 2796-2801.
doi:
10.6023/cjoc201907038
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Chauhan and coworkers reported a regioselective bromination of phenol with HBr at room temperature. The target 4-bromophenol could be obtained in 89% yield, but no experimental details could be found in the literature, see: Srivastava, S. K.; Chauhan, P. M. S.; Bhaduri, A. P. Chem. Commun. 1996, 2679 for details. We attempted for some times, but the target 3a was obtained only in low yield by using DMSO as a solvent at room temperature.
Our experimental results are consistent with Jiao's observation, ie the use of stoichiometric DMSO as the oxidant instead of as the solvent can greatly improve the reaction efficiency and selectivity, see Ref. [
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