Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2796-2801.DOI: 10.6023/cjoc201907038 Previous Articles     Next Articles



马献涛*(), 周坤洁, 任梦娟, 王梦雨, 于静   

  1. 信阳师范学院化学化工学院 信阳 464000
  • 收稿日期:2019-07-26 修回日期:2019-08-22 发布日期:2019-09-05
  • 通讯作者: 马献涛
  • 基金资助:

Steric Hindrance Effect Leading to Regioselective Bromination of Phenols with HBr

Ma Xiantao*(), Zhou Kunjie, Ren Mengjuan, Wang Mengyu, Yu Jing   

  1. College of Chemistry and Chemical Engineering, Xinyang Normal University, Xinyang 464000
  • Received:2019-07-26 Revised:2019-08-22 Published:2019-09-05
  • Contact: Ma Xiantao
  • Supported by:
    Project supported by the Key Scientific and Technological Project of Henan Province(192102310031);The Scientific Research Project of Henan Province(19B150018);The Nanhu Scholars Program for Young Scholars of Xinyang Normal University;The Young Core Instructor Program of Xinyang Normal University(2018GGJS-05)

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.

Key words: phenol, regioselective bromation, HBr, sulfoxide, steric hindrance effect