2-chloro-2,2-difluoroacetophenone: A non-ODS-based difluorocarbene precursor and its use in the difluoromethylation of phenol derivatives
2-chloro-2,2-difluoroacetophenone: A non-ODS-based difluorocarbene precursor and its use in the difluoromethylation of phenol derivatives
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2-氯-2,2-二氟苯乙酮：一种非 ODS 基二氟卡宾前体及其在苯酚衍生物二氟甲基化中的用途
DOI：
10.1021/jo061799l
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发表时间：
2006-12-22
影响因子：
3.6
通讯作者：
Hu, Jinbo
中科院分区：
文献类型：
--
作者：
Zhang, Laijun;Zheng, Ji;Hu, Jinbo
以2，2，2-三氟苯乙酮为起始原料，以高收率合成了2-氯-2，2-二氟苯乙酮（1）。发现化合物1充当良好的二氟卡宾试剂，其在氢氧化钾或碳酸钾的存在下容易与各种结构不同的苯酚衍生物4反应，以良好的产率产生芳基二氟甲基醚5。这种新的易于操作的合成方法为其他基于氟利昂或哈龙的二氟甲基化方法提供了一种环境友好的替代方法。
A novel and non-ODS-based (ODS = ozone-depleting substance) preparation of 2-chloro-2,2-difluoroacetophenone (1) was achieved in high yield by using 2,2,2-trifluoroacetophenone as the starting material. Compound 1 was found to act as a good difluorocarbene reagent, which readily reacts with a variety of structurally diverse phenol derivatives 4 in the presence of potassium hydroxide or potassium carbonate to produce aryl difluoromethyl ethers 5 in good yields. This new and easy-to-handle synthetic methodology offers an environmentally friendly alternative to other Freon- or Halon-based difluoromethylating approaches.