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

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

研究简报

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
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  • 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

  网络出版日期: 2012-02-04

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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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摘要

报道一种通过溴代和氟代的一锅法操作, 从苯乙酮直接制备α-氟代苯乙酮的新方法. 使用1,3-二溴-5,5-二甲基海因(DBDMH)作为溴代试剂, 三乙胺三氟化氢作为氟代试剂, 除了p-和m-硝基苯乙酮之外, α-氟代苯乙酮以82%～87%的收率被获得. 本方法使用的试剂价廉、收率较高、操作简单方便, 有较高的应用价值.

关键词： α-亲核氟代; α-氟代苯乙酮; 苯乙酮; 一锅法; 三乙胺三氟化氢; 1,3-二溴-5,5-二甲基海因

本文引用格式

朱伟 , 李忠洲 , 姚璐璐 , 郑祖彪 , 邹新琢 . 使用DBDMH 和Et3N·3HF 的苯乙酮一锅法α-亲核氟代[J]. 有机化学, 2012 , 32(06) : 1146 -1149 . DOI: 10.6023/cjoc1111261

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

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