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Scalable Electrochemical Reduction of Nitrobenzotrifluorides to 3-Trifluoromethylanilines
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2023-05-12 , DOI: 10.1021/acs.oprd.3c00067 Camila M. Kisukuri 1 , Johannes Seidler 1, 2 , Tobias Gärtner 2 , Denis F. Rohrmann 1 , Siegfried R. Waldvogel 1, 2, 3
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2023-05-12 , DOI: 10.1021/acs.oprd.3c00067 Camila M. Kisukuri 1 , Johannes Seidler 1, 2 , Tobias Gärtner 2 , Denis F. Rohrmann 1 , Siegfried R. Waldvogel 1, 2, 3
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The scalability of electrochemical methods remains one of the biggest reasons for their scarce implementation in manufacturing synthetic routes as well as pharmaceutical and agrochemical industry. To bridge this gap, we designed a robust and safe electrochemical workflow route for the synthesis of a collection of various 3-trifluoromethylanilines. The 3-trifluoromethylanilines are important intermediates for preparing agrochemicals and active pharmaceutical ingredients. The agent-free conversion could be easily scaled beyond the decagram scale. The cathodic conversion of nitroarenes in sulfuric acid/methanolic media was used to generate the 3-trifluoromethylanilinium bisulfates. During the reductive process, H2SO4 formed the corresponding bisulfates, which precipitated and facilitated downstream processing. The translation of a small-scale batch electrochemical reduction to forge the 3-trifluoromethylanilinium bisulfates in a continuous flow electrolysis allowed the target compound to be obtained in quantities of up to 107 g per run. The molecular composition of 3-trifluoromethylanilinium bisulfate was confirmed by elemental analysis. In addition, we demonstrated that the methodology can be extended to a broader scope. In total, eight different 3-trifluoromethylnitrobenzenes were applicable in batch, and six of them were translated to flow conditions.
中文翻译：
硝基苯并三氟化物可大规模电化学还原为 3-三氟甲基苯胺
电化学方法的可扩展性仍然是其在制造合成路线以及制药和农化行业中很少实施的最大原因之一。为了弥补这一差距，我们设计了一种稳健且安全的电化学工作流程路线，用于合成各种 3-三氟甲基苯胺。 3-三氟甲基苯胺是制备农用化学品和药物活性成分的重要中间体。无代理转换可以轻松扩展到十克规模以上。硝基芳烃在硫酸/甲醇介质中的阴极转化用于生成 3-三氟甲基苯胺硫酸氢盐。在还原过程中，H 2 SO 4形成相应的硫酸氢盐，其沉淀并有利于下游处理。通过小规模批量电化学还原在连续流动电解中锻造 3-三氟甲基苯铵硫酸氢盐，每次运行可以获得高达 107 克的目标化合物。通过元素分析证实了3-三氟甲基苯胺硫酸氢盐的分子组成。此外，我们还证明了该方法可以扩展到更广泛的范围。总共有八种不同的 3-三氟甲基硝基苯适用于批量，其中六种已转化为流动条件。
更新日期：2023-05-12
中文翻译：
硝基苯并三氟化物可大规模电化学还原为 3-三氟甲基苯胺
电化学方法的可扩展性仍然是其在制造合成路线以及制药和农化行业中很少实施的最大原因之一。为了弥补这一差距，我们设计了一种稳健且安全的电化学工作流程路线，用于合成各种 3-三氟甲基苯胺。 3-三氟甲基苯胺是制备农用化学品和药物活性成分的重要中间体。无代理转换可以轻松扩展到十克规模以上。硝基芳烃在硫酸/甲醇介质中的阴极转化用于生成 3-三氟甲基苯胺硫酸氢盐。在还原过程中，H 2 SO 4形成相应的硫酸氢盐，其沉淀并有利于下游处理。通过小规模批量电化学还原在连续流动电解中锻造 3-三氟甲基苯铵硫酸氢盐，每次运行可以获得高达 107 克的目标化合物。通过元素分析证实了3-三氟甲基苯胺硫酸氢盐的分子组成。此外，我们还证明了该方法可以扩展到更广泛的范围。总共有八种不同的 3-三氟甲基硝基苯适用于批量，其中六种已转化为流动条件。
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