Highly Selective Synthesis of 2-(2H-1,2,3-Triazol-2-yl)benzoic Acids,Organic Process Research & Development

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Highly Selective Synthesis of 2-(2H-1,2,3-Triazol-2-yl)benzoic Acids
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2019-01-18 00:00:00 , DOI: 10.1021/acs.oprd.8b00349
Remo Roth ₁ , Gunther Schmidt ₁ , Alice Prud’homme ₁ , Stefan Abele ₁

Affiliation

A selective and scalable synthesis of 2-(2H-1,2,3-triazol-2-yl)benzoic acid starting from 1-fluoro-2-nitrobenzene derivatives is presented. The four-step synthesis introduces the triazole at the start via N²-arylation of 4,5-dibromo-2H-1,2,3-triazole. A sequence of consecutive functional group transformations, namely hydrogenation, Sandmeyer iodination, and Grignard carboxylation, provides the target molecules in a reliable and scalable manner. The usefulness of this method is demonstrated by the synthesis of di- or tri(2H-1,2,3-triazol-2-yl)benzene derivatives, which are difficult to produce by other methods.

中文翻译：

2-（2 H -1,2,3-三唑-2-基）苯甲酸的高选择性合成

提出了从1-氟-2-硝基苯衍生物开始的选择性和可扩展的2-（2 H -1,2,3-三唑-2-基）苯甲酸的合成。四步合成通过4,5-二溴-2 H -1,2,3-三唑的N ^2-芳基化在开始时引入三唑。一系列连续的官能团转化，即氢化，桑德迈碘化和格利雅（Grignard）羧化反应，以可靠且可扩展的方式提供了目标分子。通过合成难以用其他方法生产的二或三（2 H -1,2,3-三唑-2-基）苯衍生物证明了该方法的有效性。

更新日期：2019-01-18

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