Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (06): 1146-1149.DOI: 10.6023/cjoc1111261 Previous Articles     Next Articles


使用DBDMH 和Et3N·3HF 的苯乙酮一锅法α-亲核氟代

朱伟, 李忠洲, 姚璐璐, 郑祖彪, 邹新琢   

  1. 华东师范大学化学系 上海 200062
  • 收稿日期:2011-11-26 修回日期:2011-12-23 发布日期:2012-02-04
  • 通讯作者: 邹新琢

One-Pot α-Nucleophilic Fluorination of Acetophenones by DBDMH and Et3N·3HF

Zhu Wei, Li Zhongzhou, Yao Lulu, Zheng Zubiao, Zou Xinzhuo   

  1. Department of Chemistry, East China Normal University, Shanghai 200062
  • Received:2011-11-26 Revised:2011-12-23 Published:2012-02-04

A novel synthetic method of α-fluoroacetophenones directly from acetophenones via one-pot reactions of bromination and fluorination is reported. Based on the nucleophilic fluorination, using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) as brominating reagent, triethylamine tris(hydrogen fluoride) as fluorinating reagent, α-fluoroacetophenones were obtained from acetophenones in 82%~87% total yields, except p- and m-nitroacetophenones. The proposed method has a high application value, because of its simplicity, low cost and good yields.

Key words: α-nucleophilic fluorination, α-fluoroacetophenones, acetophenones, one-pot, Et3N·3HF, 1,3-dibromo-5,5-dimethylhydantoin