- ACLY INHIBITORS AND USES THEREOF
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The present invention provides compounds useful as inhibitors of ATP citrate lyase (ACLY), compositions thereof, and methods of using the same.
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- Continuous production processes of dicamba methyl ester and dicamba methyl ester emulsifiable concentrate
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The invention provides a continuous production process of dicamba methyl ester. The process comprises the following steps: A) 5-bromo-3,6-dichlorosalicylic acid is subjected to a reaction under an alkaline condition and under the action of metal powder to remove bromine atoms in para-positions of hydroxyl, and 3,6-dichlorosalicylic acid is obtained; B) 3,6-dichlorosalycylic acid and halomethane are subjected to an etherification reaction in a mixed solvent of water and methanol, and methyl 3,6-dichloro-2-methoxybenzoate is obtained; C) methanol is removed by distillation; D) a system after distillation is left to stand for laying, an organic phase is distilled, and dicamba methyl ester is obtained. By means of the preparation process, continuous production can be realized, workers are notrequired to make direct contact with materials, the control degree is high, the production operation environment is greatly improved and safer, the process route and equipment are simple, the production cost is low, besides, the product yield and purity are greatly improved, and a superior route suitable for mass industrial production is provided.
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- Preparation method of dicamba
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The invention provides a preparation method of dicamba. The preparation method comprises the steps as follows: A) salicylic acid and bromine or hydrogen bromide are subjected to a reaction in concentrated sulfuric acid, 5-bromosalicylic acid is obtained; B) 5-bromosalicylic acid and chlorine are subjected to a chlorination reaction, 5-bromo-3,6-dichlorosalycylic acid is obtained; C) 5-bromo-3,6-dichlorosalycylic acid is subjected to a debromination reaction under the alkaline condition and under the action of metal powder, and 3,6-dichlorosalycylic acid is obtained; D) 3,6-dichlorosalycylic acid and halomethane are subjected to an etherification reaction in a mixed solvent of water and methanol, and methyl-3,6-dichloro-2-methoxybenzoate is obtained; E) methanol is removed by distillation;F) a system after distillation is left to stand for laying, an organic phase is distilled, and dicamba methyl ester is obtained; G) dicamba methyl ester is subjected to alkaline hydrolysis, acidification and drying, and dicamba is obtained. The route comprises few steps and has low difficulty, the equipment requirement and investment are lower, continuous production can be realized, no three wastes are produced, and the product yield and purity are higher.
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- Preparation method of micamba methyl ester
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The invention provides a preparation method of micamba methyl ester. The preparation method comprises the steps as follows: A) salicylic acid and bromine are subjected to a reaction in concentrated sulfuric acid, 5-bromosalicylic acid is obtained; B) 5-bromosalicylic acid and chlorine are subjected to a chlorination reaction, 5-bromo-3,6-dichlorosalycylic acid is obtained; C) 5-bromo-3,6-dichlorosalycylic acid is subjected to a debromination reaction under the alkaline condition and under the action of metal powder, and 3,6-dichlorosalycylate is obtained; D) 3,6-dichlorosalycylate and halomethane are subjected to a methylation reaction in methanol and a quaternary ammonium salt phase transfer catalyst, and 3,6-dichloro-2-methyl methoxybenzoate is obtained; E) methanol is removed by distillation; F) a system after distillation is left to stand for laying, an organic phase is distilled, and dicamba methyl ester is obtained. By means of the preparation method, the yield and purity are higher, the route is simple and the production cost is low.
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- Total recycling method of salicylic acid in preparation process of 3,6-dichlorosalicylic acid
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The invention provides a total recycling method of salicylic acid in a preparation process of 3,6-dichlorosalicylic acid. The method comprises steps as follows: A), salicylic acid is subjected to reaction with bromine or hydrogen bromide in concentrated sulfuric acid, 5-bromosalicylic acid is obtained; B), 5-bromosalicylic acid is subjected to chlorination with chlorine, and 5-bromo-3,6-dichlorosalicylic acid is obtained; C), 5-bromo-3,6-dichlorosalicylic acid is subjected to debromination reaction under the action of a catalyst, and crude 3,6-dichlorosalicylic acid is obtained; D), crude 3,6-dichlorosalicylic acid is recrystallized in xylene or toluene, and pure 3,6-dichlorosalicylic acid and an impurity-containing solvent are obtained, wherein impurities comprise 3-chlorosalicylic acid,3,5-dichlorosalicylic acid and 3-bromo-6-chlorosalicylic acid; E), the impurity-containing solvent is subjected to alkali washing, a water phase is obtained by liquid separation, a catalyst is added to the water phase for hydrogenation dehalogenation reaction, filtering is performed to remove the catalyst, the filtrate is acidified, and salicylic acid is obtained and recycled to step A). Total recycling of salicylic acid is realized, and the environmental benefit is high.
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- Preparation method of 3,6-dichlorosalicylic acid
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The invention provides a preparation method of 3,6-dichlorosalicylic acid. The method comprises the following steps: 5-bromo-3,6-dichlorosalicylic acid is subjected to debromination reaction in the alkaline condition and under action of metal powder, and 3,6-dichlorosalicylic acid is obtained. 5-bromo-3,6-dichlorosalicylic acid is subjected to selective debromination reaction in the alkaline condition and under action of metal powder, the reaction has high selectivity, the conversion rate is high, the reaction rate is high, and the prepared product has high purity. The process route is simple,equipment is conventional, the metal powder is easy to recycle, and the cost is low.
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- A new process to prepare 3,6-dichloro-2-hydroxybenzoic acid, the penultimate intermediate in the synthesis of herbicide dicamba
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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.
- Walker, Daniel P.,Harris, G. Davis,Carroll, Jeffery N.,Boehm, Terri L.,McReynolds, Matthew D.,Struble, Justin R.,van Herpt, Jochem,van Zwieten, Don,Koeller, Kevin J.,Bore, Mangesh
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p. 1032 - 1036
(2019/03/17)
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- 3,6-DICHLOROSALICYLIC ACID COMPOUNDS AND RELATED SYNTHETIC PROCESSES
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The present disclosure relates, in general, to 5-halo-3,6-dichlorosalicylic acid compounds, 5-halo-3,6-dichlorosalicyaldehyde compounds, processes for preparing 5-halo-3,6-dichlorosalicylic acid compounds, processes for preparing 5-halo-3,6- dichlorosalicyaldehyde compounds, processes for preparing 3,6-dichlorosalicylic acid compounds, and processes that employ such compounds as intermediates in the preparation of the herbicide dicamba.
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Paragraph 0142
(2016/01/26)
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