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Preparation method of 2, 6-dihalogenated methyl benzoate

A technology of methyl dihalogenated benzoate and dihalogenated benzoic acid is applied in the field of preparation of methyl 2,6-dihalogenated benzoate, and can solve the problem that it is difficult to realize large-scale production and application and the environmental pollution of the generation process. , the complex reaction device and other problems, to achieve the effect of easy reaction operation and purification process, high reaction yield and simple reaction device

Pending Publication Date: 2022-03-15
维思普新材料(苏州)有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The invention provides a kind of preparation method of 2,6-dihalobenzoic acid methyl ester, and its purpose is in order to solve the safety of the reagent used in the preparation process of 2,6-dihalobenzoic acid esterification in the prior art (personal injury) and environmental safety), production process environmental pollution and hazards, raw material costs, complex reaction devices (such as microwave equipment), and other issues that make it difficult to achieve large-scale production and application

Method used

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  • Preparation method of 2, 6-dihalogenated methyl benzoate
  • Preparation method of 2, 6-dihalogenated methyl benzoate
  • Preparation method of 2, 6-dihalogenated methyl benzoate

Examples

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Embodiment 1

[0036] Preparation method of 2,6-dichlorobenzoate methyl ester, specific synthetic route figure 1 Indicated.

[0037] 1) 2,6-dichlorobenzoic acid (38.2 g, 200 mmol), dimethyl carbonate (305.6 g), and triamiacarbonate (35.6 g) and triamiacarbonate ( Dabco, 22.4 g, 200 mmol, stirred at room temperature. The temperature was warmed to 90 ° C, and the insulation reaction was 10 h.

[0038] 2) After the reaction is completed, stop heating, and the reaction is cooled to room temperature. The solvent was evaporated under reduced pressure, and 152.8 g of water was added to the residual liquid, stirred vigorously, extracted with ethyl acetate. Ethyl acetate layer is sequentially with water, dilute hydrochloric acid (5%), saturated sodium hydrogencarbonate, and water, the organic phase is dried and concentrated, that is, 2,6-dichlorobenzoate, weight of about 40g. 97.5% yield, the content is 98.680%, and the results are Figure 4 Indicated. 1 H NMR (400MHz, CDCL 3 : Δ7.33-7.20 (m, 3H), 3.97 (S...

Embodiment 2

[0040] Method for preparing 2-bromo-6-fluorobenzoate methyl ester, specific synthetic route figure 2 Indicated.

[0041] 1) 2-bromo-6-fluorobenzoic acid (43.8 g, 200 mmol), dimethyl carbonate (305.6 g) and DABCO (22.4 g) were sequentially added to the 1L tetra-necked flask equipped with a stirrer, reflow tube, and thermometer. , 200 mmol), stirred at room temperature. The temperature was warmed to 90 ° C, and the insulation reaction was 10 h.

[0042] 2) After the reaction is completed, stop heating, and the reaction is cooled to room temperature. The solvent was evaporated under reduced pressure, and 152.8 g of water was added to the residual liquid, stirred vigorously, extracted with ethyl acetate. Ethyl acetate layer is sequentially with water, dilute hydrochloric acid (5%), saturated sodium hydrogencarbonate, and water, the organic phase is dried, and then the pale yellow oily liquid, i.e., 2-bromo-6-fluorobenzoate, weighs about 45g. 96.5% yield, the content is 98.257%, the re...

Embodiment 3

[0044] Method for preparing 2,6-difluorobenzoate methyl ester, specific synthetic route image 3 Indicated.

[0045] 1) 2,6-difluorophenyl (31.6 g, 200 mmol), dimethyl carbonate (305.6 g) and Dabco (22.4 g) were sequentially added to the 1L tetra-neck flask equipped with a stirrer, reflow tube and a thermometer. 200 mmol), stirred at room temperature. The temperature was warmed to 90 ° C, and the insulation reaction was 10 h.

[0046] 2) After the reaction is completed, stop heating, and the reaction is cooled to room temperature. The solvent was evaporated under reduced pressure, and 152.8 g of water was added to the residual liquid, stirred vigorously, extracted with ethyl acetate. Ethyl acetate layer is sequentially with water, dilute hydrochloric acid (5%), saturated sodium hydrogencarbonate, and water, the organic phase is dried and concentrated, that is, 2,6-difluorobenzoate, weight of about 33.3g. 96.8% yield, the content is 98.895%, the result is like Figure 8 Indicated. 1 ...

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Abstract

The invention provides a preparation method of 2, 6-dihalogenated methyl benzoate, which comprises the following steps: 1) mixing 2, 6-dihalogenated benzoic acid with dimethyl carbonate, adding DABCO, fully stirring, and heating for reaction; and 2) after the reaction is finished, stopping heating, naturally cooling, evaporating to remove the solvent under reduced pressure, adding water into residues, extracting, washing, drying, and evaporating to remove an organic phase under reduced pressure to obtain the 2, 6-dihalogenated methyl benzoate. The preparation method disclosed by the invention has the characteristics of low toxicity, environmental protection, high reaction yield, small environmental pollution and the like, and has a good industrial application prospect; the 2, 6-dihalogenated methyl benzoate prepared by the invention has important application in the aspects of research and development of new drugs and preparation of functional materials.

Description

Technical field [0001] The present invention relates to the field of organic synthesis, and more particularly to the preparation method of 2,6-dihalogenated benzoate. Background technique [0002] The esterification reaction is a relatively basic reaction type in organic synthesis. With the continuous advancement of organic synthesis, the esterification reaction conditions for different types of substrates are also increasingly enriched (Esterification: Methods, Reactions, And Applications.john Wiley & Sons, 2009.). Most of the common esterification reactions currently reported requires strong acid (such as sulfuric acid, hydrochloric acid), toxic chemicals (methyl iodide or dimethyl sulfate) or hazardous chemicals (diazolin). [0003] 2,6-dihalogenated benzoic acid is a class of carboxylic acid derivatives having special structures. On the one hand, the halogen atom relatively strong pull electrical effect enhances the acidicity of mother-core benzoic acid, and two of the carbox...

Claims

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Application Information

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IPC IPC(8): C07C67/02C07C67/58C07C67/48C07C69/78
CPCC07C67/02C07C67/58C07C67/48C07C69/78
Inventor 刘向阳张业欣袁晓冬陈华
Owner 维思普新材料(苏州)有限公司
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