Method for synthesizing methyl 3-(trifluoromethyl)benzoate

A technology of methyl trifluoromethyl benzoate and trifluoromethyl benzoyl, which is applied in the field of synthesis of methyl m-trifluoromethyl benzoate and ester compounds, and can solve complex process routes and low reaction conversion rates And the problems of low product yield and difficulty in industrialization, etc., to achieve the effect of high reaction yield, increased feasibility, and simple operation

Inactive Publication Date: 2012-02-15
ZHEJIANG WEIHUA CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In summary, the prior art and synthetic routes mainly have the following problems in the process of preparing methyl m-trifluoromethylbenzoate (I): 1. The raw materials are relatively expensive, resulting in excessively high produ

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] The preparation of embodiment 1 m-trichloromethylbenzoyl chloride

[0042] In a 500mL four-neck flask equipped with an electric stirrer, a temperature measuring thermometer, a reflux condenser and a chlorine port, add a specified amount of m-toluoyl chloride 200ml and a solvent 200ml, and add an appropriate amount of cocatalyst DMF0.2ml while stirring . Place the LED light source about 10cm away from the four-necked flask, slowly raise the temperature to 125°C, control the temperature at 120°C~135°C, then slowly introduce chlorine gas dried with concentrated sulfuric acid, and adjust the flow rate of chlorine gas so that it does not disappear in the tail gas Yellow-green color is suitable, the reaction tail gas is absorbed by water and dilute lye successively, and the reaction process and reaction end point are tracked by gas chromatography. After the reaction is completed, the solvent is removed to obtain the m-trichloromethylbenzoyl chloride intermediate, and the sol...

Embodiment 2

[0043] The preparation of embodiment 2 m-trifluoromethylbenzoyl fluoride

[0044] Add m-trichloromethylbenzoyl chloride 400g and catalyzer 0.2g in the 1000ml high-pressure reaction kettle that is equipped with electric stirrer, temperature measuring device, reflux condenser and pressure relief device through pressure test, airtight reaction kettle, use nitrogen pressure Add 200 g of anhydrous hydrogen fluoride. Slowly raise the temperature, and the pressure in the kettle will also increase during the heating process. When the pressure in the kettle reaches 2.0-2.2Mpa, the hydrogen chloride gas generated by the reaction will be discharged out of the reactor through the pressure relief valve, and this pressure will be maintained throughout the process. The discharged hydrogen chloride and entrained hydrogen fluoride are recycled and absorbed with water. Then raise the temperature by 120-130°C, maintain the temperature and pressure, keep it warm for about 2 hours, take samples, ...

Embodiment 3

[0045] The preparation of embodiment 3 m-trifluoromethylbenzoic acid methyl ester

[0046] In a four-necked flask equipped with a reflux condenser, a thermometer, an electric stirrer and a dropping funnel, add 360ml of methanol and 70g of light calcium carbonate. Open the cooling water of the reflux condenser, keep the internal temperature of the four-necked flask at 40-45°C, and slowly add m-trifluoromethylbenzoyl fluoride 220g dropwise therein through the dropping funnel, at this moment, the system emits a large amount of carbon dioxide gas and Heat to control the rate of addition of m-trifluoromethylbenzoyl fluoride. After the addition was completed, the system was incubated and reacted at the reflux temperature of methanol for 2 hours, and the substrate was detected by chromatography until the reaction was completed. Cool and filter to remove the fluoride salt, wash the fluoride salt with a small amount of methanol, and combine the organic phases.

[0047] The methanol w...

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PUM

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Abstract

The invention provides a new method for synthesizing methyl 3-(trifluoromethyl)benzoate, which comprises side-chain chlorination reaction, fluorination reaction and esterification reaction. The method is environment-friendly and high in reaction yield; and the selected raw materials, namely chlorine, m-methylbenzoyl chloride, anhydrous hydrofluoric acid, methanol, light calcium carbonate and the like are cheap and readily available in industry. The related three reactions are high in controllability and easy to operate, and an intermediate product is not required to be purified and can undergo the next reaction. Byproducts generated in the reactions can be effectively utilized, and the industrial feasibility of the method is improved.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and relates to a synthetic method for preparing trifluoromethylbenzene ester compounds, in particular to a method for preparing methyl m-trifluoromethylbenzoate. Background technique [0002] Methyl m-trifluoromethyl benzoate is an important pesticide intermediate for the preparation of urea compounds with insecticidal activity, such as the urea insecticide metaflumizone; methyl m-trifluoromethyl benzoate It is also the main raw material for the preparation of high-purity m-trifluoromethylbenzoic acid. Methyl m-trifluoromethylbenzoate has a variety of preparation methods, and the general synthesis method is to use a relatively low content of m-trifluoromethylbenzoic acid as a raw material, and carry out esterification with anhydrous methanol under the action of concentrated sulfuric acid reaction to synthesize. However, this method often brings many problems such as high production co...

Claims

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Application Information

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IPC IPC(8): C07C69/78C07C67/08
Inventor 陈静华吴江伟王凯泉赵红英常绚超
Owner ZHEJIANG WEIHUA CHEMICAL CO LTD
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