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A new process to prepare 3,6-dichloro-2-hydroxybenzoic acid, the penultimate intermediate in the synthesis of herbicide dicamba
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2019-03-09 , DOI: 10.1016/j.tetlet.2019.03.024
Daniel P. Walker , G. Davis Harris , Jeffery N. Carroll , Terri L. Boehm , Matthew D. McReynolds , Justin R. Struble , Jochem van Herpt , Don van Zwieten , Kevin J. Koeller , Mangesh Bore

Glyphosate [N-(phosphonomethyl)glycine] is a broad spectrum, post-emergent herbicide that is among the most widely used agrochemicals globally. Over the past 30 years, there has been a development of glyphosate-resistant weeds, which pose a significant challenge to growers and crop scientists, resulting in lower crop yields and increased costs. 3,6-Dichloro-2-methoxybenzoic acid (dicamba) is the active ingredient in XtendiMax®, a standalone herbicide developed by Bayer Crop Science to control broadleaf weeds, including glyphosate-resistant species. 3,6-Dichloro-2-hydroxybenzoic acid (3,6-DCSA) is the penultimate intermediate in the synthesis of dicamba. Existing dicamba manufacturing routes utilize a high temperature, high pressure Kolbe-Schmitt carboxylation to prepare 3,6-DCSA. Described in this Letter is a new, non-Kolbe-Schmitt process to prepare 3,6-DCSA from salicylic acid in four chemical steps.



中文翻译:

制备3,6-二氯-2-羟基苯甲酸的新方法,这是合成除草剂麦草畏的倒数第二个中间体

草甘膦[ N-(膦酰基甲基)甘氨酸]是一种广谱的芽后除草剂,是全球使用最广泛的农用化学品之一。在过去的30年中,抗草甘膦的杂草得到了发展,这对种植者和农作物科学家构成了巨大的挑战,导致农作物产量降低和成本增加。3,6-二氯-2-甲氧基苯甲酸(麦草畏)是XtendiMax®的活性成分,XtendiMax®是拜耳作物科学公司开发的用于控制阔叶杂草(包括抗草甘膦的物种)的独立除草剂。3,6-二氯-2-羟基苯甲酸(3,6-DCSA)是麦草畏合成中的倒数第二个中间体。现有的麦草畏制造路线利用高温高压Kolbe-Schmitt羧化反应制备3,6-DCSA。这封信中描述的是一种新的非柯尔布-施密特流程,该流程准备3,

更新日期:2019-03-09
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