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A kind of synthetic method of m-trifluoromethylacetophenone

A technology of trifluoromethyl acetophenone and trifluoromethyl aniline, applied in the synthesis field of m-trifluoromethyl acetophenone, can solve the problems of high risk, high raw material price, difficult industrialization and the like, and achieves high quality and Stable performance, low impurity content, safe and controllable method

Active Publication Date: 2015-09-09
ZHEJIANG WEIHUA NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The first three methods have difficult sources of raw materials, high risk, and are not easy to industrialize; the last method is easier to industrialize, but the raw materials used are expensive and not competitive

Method used

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  • A kind of synthetic method of m-trifluoromethylacetophenone

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Embodiment 1

[0026] A method for synthesizing m-trifluoromethyl acetophenone, using m-trifluoromethyl aniline as a starting material, and the specific steps include:

[0027] (1) Diazotization reaction

[0028] 46 g of m-trifluoromethyl aniline was slowly added to a four-necked flask containing 280 g of sulfuric acid solution (mass concentration 20%), then cooled to 0℃ and started to add 30% NaNO dropwise 2 Aqueous solution of 72 g, temperature controlled at 0~5°C, kept and stirred for 1 hour after dripping, to prepare a pale yellow diazonium salt clear liquid, keep it for use.

[0029] (2) Coupling reaction

[0030] Add 4.2 g of cuprous chloride, 10.2 g of acetic acid, 50.5 g of 50% acetaldoxime aqueous solution and 100 mL of toluene into the four-necked flask, stir and cool. After cooling to below 5℃, start to add the above-mentioned diazonium salt clear liquid dropwise, and at the same time add 30% liquid caustic soda, control the pH at 4~4.5, and the temperature at 0~5℃. After the addition, t...

Embodiment 2

[0034] (1) Diazotization reaction

[0035] 46 g m-trifluoromethyl aniline was slowly added to a four-necked flask containing 280 g sulfuric acid solution (mass concentration 25%), then cooled to 0°C and started to add 30% NaNO dropwise 2 Aqueous solution of 71 g, control the temperature at 0~5℃, keep and stir for 1 hour after dripping, to prepare a pale yellow diazonium salt clear liquid, keep it for use.

[0036] (2) Coupling reaction

[0037] Add 8.6 g of copper acetate, 5.2 g of acetic acid, 45.5 g of 50% acetaldoxime aqueous solution and 100 mL of toluene into the four-neck flask, stir and cool. After cooling to below 5℃, start to add the above-mentioned diazonium salt clear liquid dropwise, and at the same time add 30% liquid caustic soda, control the pH at 4~4.5, and the temperature at 0~5℃. After the addition, the temperature was raised to 15°C and stirred, followed by GC analysis. After the reaction, the layer was allowed to stand for separation, and the upper organic phase ...

Embodiment 3

[0041] A method for synthesizing m-trifluoromethyl acetophenone, using m-trifluoromethyl aniline as a starting material, and the specific steps include:

[0042] (1) Diazotization reaction

[0043] 46 g m-trifluoromethyl aniline was slowly added to a four-necked flask containing 280 g sulfuric acid solution (mass concentration 25%), then cooled to 0°C and started to add 30% NaNO dropwise 2 Aqueous solution of 72 g, temperature controlled at 0~5°C, kept and stirred for 1 hour after dripping, to prepare a pale yellow diazonium salt clear liquid, keep it for use.

[0044] (2) Coupling reaction

[0045] Add 3.9 g of copper chloride, 8.0 g of acetic acid, 48.5 g of 50% acetaldoxime aqueous solution and 100 mL of toluene into the four-neck flask, stir and cool. After cooling to below 5℃, start to add the above-mentioned diazonium salt clear liquid dropwise, and at the same time add 30% liquid caustic soda, control the pH at 4~4.5, and the temperature at 0~5℃. After the addition, the temper...

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Abstract

The invention discloses a method for synthesizing m-trifluoromethyl acetophenone which is an important intermediate for medicine, pesticide and pigment. According to the method, m-trifluoromethylaniline as the initial raw material is diazotized to prepare a diazonium salt which is coupled with acetaldoxime under the catalysis of a copper salt by controlling the pH value at 4-4.5 and the temperature at 0-5 DEG C, and the coupling compound is extracted by an organic solvent and then hydrolyzed by using hydrochloric acid to obtain the m-trifluoromethyl acetophenone. The total yield of the m-trifluoromethyl acetophenone produced according to the method is more than 70 percent; and the reaction conditions of the method are simple, the yield is high, the pollution is small, and the method is applied to industrial production.

Description

Technical field [0001] The invention belongs to the field of chemical synthesis, and is specifically a synthesis method of m-trifluoromethylacetophenone. Background technique [0002] 3'-(Trifluoromethyl)acetophenone), referred to as TFAP, is a light yellow liquid and is mainly used in the fields of medicine, pesticides and dyes. It is a key intermediate in the synthesis of the methoxypropylene ester compound trifloxystrobin (trade name Flint), and is also an important raw material for the synthesis of medicines and dyes. Its key downstream product, trifloxystrobin, is a new type of highly efficient, safe and broad-spectrum fungicide that has special effects on powdery mildew and leaf spot. It is also effective against rust, downy mildew, damping off, apple scab, etc. It has good activity, low toxicity to mammals, bees, birds, fish, insects, etc., and has rapid environmental metabolism, so it is safe for the environment, has no teratogenic, carcinogenic, or mutagenic effect...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/80C07C45/42
Inventor 李俊奇周洪钟陈静华张泉泉王国荣常绚超葛天权
Owner ZHEJIANG WEIHUA NEW MATERIAL CO LTD
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