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2-Chloro-2,2-difluoroacetophenone: A Non-ODS-Based Difluorocarbene Precursor and Its Use in the Difluoromethylation of Phenol Derivatives
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2006-11-24 00:00:00 , DOI: 10.1021/jo061799l
Laijun Zhang 1 , Ji Zheng 1 , Jinbo Hu 1
Affiliation  

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.

中文翻译:

2-氯-2,2-二氟苯乙酮:一种非基于ODS的二氟卡宾前体及其在苯酚衍生物的二氟甲基化中的应用

以2,2,2-三氟苯乙酮为起始原料,高收率地获得了一种新型的,基于非ODS的(ODS =消耗臭氧层物质)2-氯-2,2-二氟苯乙酮(1)的制备方法。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易于与多种结构多样的酚衍生物4反应,以高收率生产芳基二氟甲基醚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。
更新日期:2006-11-24
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