Homocoupling of a Grignard Reagent toward the Synthesis of 2,2′-Bis(trifluoromethyl)-4,4′-diaminobiphenyl,Organic Process Research & Development

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Homocoupling of a Grignard Reagent toward the Synthesis of 2,2′-Bis(trifluoromethyl)-4,4′-diaminobiphenyl
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2021-10-19 , DOI: 10.1021/acs.oprd.1c00227
Jiro Nakatani ₁ , Tatsuhiro Nozoe ₁

Affiliation

A new process for the synthesis of 2,2′-bis(trifluoromethyl)-4,4′-diaminobiphenyl (TFMB) comprising three steps has been industrially developed. The first step is the homocoupling of the Grignard reagent derived from 1-chloro-2-(trifluoromethyl)benzene with iron chloride(III) in the presence of an oxidizing agent to afford 2,2′-bis(trifluoromethyl)biphenyl. The second step is the nitration of this biphenyl to 2,2′-bis(trifluoromethyl)-4,4′-dinitrobiphenyl, and the third step is the reduction of this dinitrobiphenyl using hydrogen over Pd/C to afford TFMB. This process has been demonstrated on an industrial scale.

中文翻译：

用于合成 2,2'-双(三氟甲基)-4,4'-二氨基联苯的格氏试剂的同源偶联

工业上开发了一种合成 2,2'-双(三氟甲基)-4,4'-二氨基联苯 (TFMB) 的新工艺，包括三个步骤。第一步是在氧化剂存在下将源自 1-氯-2-（三氟甲基）苯的格氏试剂与氯化铁（III）均偶联，得到 2,2'-双（三氟甲基）联苯。第二步是将该联苯硝化为 2,2'-双（三氟甲基）-4,4'-二硝基联苯，第三步是使用氢气在 Pd/C 上还原该二硝基联苯以提供 TFMB。该方法已在工业规模上得到证明。

更新日期：2021-11-19

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