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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 06: 1146 - 1149

DOI: https://doi.org/10.6023/cjoc1111261

Notes

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

  • Zhu Wei ,
  • Li Zhongzhou ,
  • Yao Lulu ,
  • Zheng Zubiao ,
  • Zou Xinzhuo
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  • Department of Chemistry, East China Normal University, Shanghai 200062

Received date: 2011-11-26

  Revised date: 2011-12-23

  Online published: 2012-02-04

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Abstract

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

Cite this article

Zhu Wei , Li Zhongzhou , Yao Lulu , Zheng Zubiao , Zou Xinzhuo . One-Pot α-Nucleophilic Fluorination of Acetophenones by DBDMH and Et3N·3HF[J]. Chinese Journal of Organic Chemistry, 2012 , 32(06) : 1146 -1149 . DOI: 10.6023/cjoc1111261

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