Method for preparing 2,3,4,5-tetrafluoro methyl benzoate in series reaction

A technology of methyl tetrafluorobenzoate and tetrachlorophthalic anhydride, applied in the field of fine chemical synthesis, can solve problems such as high cost, large environmental pollution, long process route, etc. good performance

Active Publication Date: 2012-07-25
浙江东晖药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above-mentioned process route is long, the cost is high, and the environmental pollution is relatively large.

Method used

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  • Method for preparing 2,3,4,5-tetrafluoro methyl benzoate in series reaction

Examples

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Embodiment 1

[0028] Example 1: 286 grams (1 mole) of 2,3,4,5-tetrachlorobenzoic anhydride, 232 grams (4 moles) of potassium fluoride, 1-butyl-3-methylimidazole tetrafluoroborate 858 grams, 14.3 grams of the magnetic solid base catalyst obtained in Example 1 was added to the reaction flask, and after reacting at 80°C for 5 hours, the reaction solution was cooled, 96 grams (2 moles) of methanol was added, and the reaction was carried out at 60°C for 10 hours. After the reaction, the reaction solution was extracted with toluene and distilled to obtain 199 g of methyl 2,3,4,5-tetrafluorobenzoate, with a yield of 96%, a boiling point of 220-249°C, and a melting point of 126-128°C. Content ≥ 99.5%.

[0029] The solid base catalyst used in the present invention is a magnetic solid base catalyst, and its preparation method refers to "Preparation and Characterization of Magnetic Magnesium Aluminum Hydrotalcite Solid Base", Volume 29, No. 3 (March 2002) of Applied Science and Technology.

[0030] I...

Embodiment 2

[0031]Example 2: 286 grams (1 mole) of 2,3,4,5-tetrachlorobenzoic anhydride, 630 grams of sodium fluoride, 5720 grams of 1-pentyl-3-methylimidazolium hexafluorophosphate, magnetic solid Add 42.9 grams of alkali catalyst into the reaction flask, react at 20°C for 15 hours, cool the reaction solution to room temperature, add 160 grams (5 moles) of methanol, and react at 30°C for 15 hours. After extraction and distillation, 194.8 g of methyl 2,3,4,5-tetrafluorobenzoate was obtained, with a yield of 94%, a boiling point of 220-249°C, a melting point of 126-128°C, and a content of 99.3%.

Embodiment 3

[0032] Example 3: 286 grams (1 mole) of 2,3,4,5-tetrachlorobenzoic anhydride, 608 grams (4 moles) of cesium fluoride, and 5000 grams of 1-nonyl-3-methylimidazole acetate , 2.86 grams of magnetic solid base catalyst, added to the reaction bottle, reacted at 150 ° C for 2 hours, cooled the reaction solution, added 32 grams (1 mole) of methanol, and reacted at 100 ° C for 1 hour. After the reaction, the reaction solution was used After toluene extraction and distillation, 190.7 g of methyl 2,3,4,5-tetrafluorobenzoate was obtained, with a yield of 92%, a boiling point of 220-249°C, a melting point of 126-128°C, and a content of 99.2%.

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Abstract

The invention discloses a method for preparing 2,3,4,5-tetrafluoro methyl benzoate in series reaction, belonging to the technical field of fine chemical synthesis. The method comprises the following steps: carrying out fluorination reaction at 20-150 DEG C for 1-15 hours using ionic liquid, fluoride, a solid base catalyst and 2,3,4,5-tetrachlorophthalic anhydride, cooling the reaction solution to room temperature after the reaction is complete, adding methanol to perform esterification and decarboxylation reaction, and carrying out post treatment to obtain 2,3,4,5-tetrafluoro methyl benzoate. The preparation method provided by the invention uses ionic liquid and magnetic solid base catalyst, and performs series reaction between various components; the method is simple in operation, convenient in post treatment, good in technical performance, and low in environmental pollution; the yield of the obtained 2,3,4,5-tetrafluoro methyl benzoate is above 92%, and the content is >= 99.2%. The method is a green chemical synthesis technology and is suitable for industrialized production.

Description

technical field [0001] The present invention belongs to the technical field of fine chemical synthesis, and specifically relates to a method for preparing methyl tetrafluorobenzoate by applying heterogeneous catalytic series reaction technology in ionic liquid medium. Background technique [0002] Methyl 2,3,4,5-tetrafluorobenzoate is an important drug intermediate, mainly used in the synthesis of third-generation quinolones [lomefloxacin, ofloxacin, p. Fourth-generation quinolones (levofloxacin, sparfloxacin). It is also widely used in synthetic resins, conductive materials and liquid crystal materials. The earliest synthesis of methyl tetrafluorobenzoate can be traced back to the 1920s, mainly using tetrachlorophthalic acid as raw material through the imide route (including imidization, fluorination, hydrolysis, decarboxylation and esterification). Step reaction) and synthesized by acid chloride route (including hydrolysis, acid chloride, fluorination, hydrolysis, decarb...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/78C07C67/08
Inventor 陈熙强王勇裴文
Owner 浙江东晖药业有限公司
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