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 shu

Steric Hindrance Effect Leading to Regioselective Bromination of Phenols with HBr

College of Chemistry and Chemical Engineering, Xinyang Normal University, Xinyang 464000

Corresponding author: Ma Xiantao, xiantaoma@126.com
Received Date: 26 July 2019
Revised Date: 22 August 2019
Available Online: 5 October 2019
Fund Project: Project supported by the Key Scientific and Technological Project of Henan Province (No. 192102310031), the Scientific Research Project of Henan Province (No. 19B150018), the Nanhu Scholars Program for Young Scholars of Xinyang Normal University and the Young Core Instructor Program of Xinyang Normal University (No. 2018GGJS-05)the Key Scientific and Technological Project of Henan Province 192102310031the Young Core Instructor Program of Xinyang Normal University 2018GGJS-05the Scientific Research Project of Henan Province 19B150018

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A mild and regioselective bromination of phenols with the cheap and easily-available HBr is developed. By replacing the common used dimethyl sulfoxide (DMSO) with sulfoxides bearing sterically hindered substituents, the desired brominated phenols could be obtained in moderate to high yields with up to 99/1 regioselectivity. This method could be easily scaled up to 50 mmol scale and has the potential to isolate the desired product by simple extraction and recrystallization, showing great practicality of this new method.
- phenol,
- regioselective bromation,
- HBr,
- sulfoxide,
- steric hindrance effect
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