A kind of preparation method of difluoropiperone

A difluoro piperonyl ring and piperonyl ring technology, applied in the direction of organic chemistry and the like, can solve the problems of difficult recycling of sulfolane, poor atom economy, long reaction time, etc., and achieve good heat exchange efficiency, low pollution, and safe and controllable reaction. Effect

Active Publication Date: 2021-01-29
XIAN MODERN CHEM RES INST
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  • Description
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Problems solved by technology

The fluorine-chlorine exchange method is a classic method for fluorine atoms on compounds. Its disadvantage is that the atom economy is poor, and it takes two steps to get the product.
Chlorination reagents such as chlorine gas, phosphorus pentachloride, phosphorus trichloride and other chlorination reagents are needed in the synthesis and chlorination process of difluoropiperone ring, resulting in long reaction time, complicated post-treatment, and large waste gas output
The fluorination process needs to use potassium fluoride, triethylamine hydrogen fluoride as fluorine source, high boiling point solvent sulfolane, etc. The reaction time is long and the temperature is high, resulting in a large amount of salt in the post-treatment, and the sulfolane is difficult to recycle.

Method used

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  • A kind of preparation method of difluoropiperone
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  • A kind of preparation method of difluoropiperone

Examples

Experimental program
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Embodiment 1

[0021] Weigh 100g of piperonylcycline and 900g of acetonitrile, mix and prepare a 10% piperonine in acetonitrile solution, then add 1g of trifluoroacetic acid, mix well and set aside.

[0022] Adjust the flow rate of fluorine gas and nitrogen gas to prepare a mixed gas of fluorine gas and nitrogen gas with a mass fraction of 10% for use.

[0023] use as figure 1 In the reaction process shown, the microchannel reactor made of silicon carbide is selected, the liquid holding capacity of each module is 1ml, the reaction temperature of the module is set at -20°C, the pumping rate is controlled to adjust the reaction residence time, and the residence time is set at 20s , the A module is continuously and uniformly pumped into the piperonine acetonitrile solution (containing 1% trifluoroacetic acid) with a mass fraction of 10% for precooling, while the B module is continuously and uniformly fed with a mass fraction of 10% fluorine-nitrogen mixed gas, and its fluorine The molar amount...

Embodiment 2

[0025] Weigh 150g of piperonylcycline and 850g of acetonitrile, mix and prepare a 10% piperonine in acetonitrile solution, then add 1g of trifluoromethanesulfonic acid, mix well and set aside.

[0026] Adjust the flow rate of fluorine gas and nitrogen gas to prepare a mixed gas of fluorine gas and nitrogen gas with a mass fraction of 50% for use.

[0027] use as figure 1 In the reaction process shown, the microchannel reactor made of silicon carbide is selected, the liquid holding capacity of each module is 1ml, the reaction temperature of the module is set at -40°C, the pumping rate is controlled to adjust the reaction residence time, and the residence time is set at 10s , A module is continuously and uniformly pumped into a piperonine acetonitrile solution (containing 1% trifluoromethanesulfonic acid) with a mass fraction of 15% for precooling, while the B module is continuously and uniformly fed with a mass fraction of 50% fluorine-nitrogen mixed gas, The molar amount of f...

Embodiment 3

[0029] Weigh 100 g of piperonylcycline and 900 g of formic acid, mix and prepare a piperonylcycline formic acid solution with a mass fraction of 10%, then add 0.5 g of trifluoromethanesulfonic acid, mix well and set aside.

[0030] Adjust the flow rate of fluorine gas and nitrogen gas to prepare a mixed gas of fluorine gas and nitrogen gas with a mass fraction of 10% for use.

[0031] use as figure 1 In the reaction process shown, the microchannel reactor made of silicon carbide is selected, the liquid holding capacity of each module is 1ml, the reaction temperature of the module is set at -10°C, the pumping rate is controlled to adjust the reaction residence time, and the residence time is set at 30s , A module is continuously and uniformly pumped into a piperonine solution (containing 0.5% trifluoromethanesulfonic acid) with a mass fraction of 10% for precooling, while the B module is continuously and uniformly fed with a mass fraction of 10% fluorine-nitrogen mixed gas, Th...

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Abstract

The present invention relates to a preparation method of a drug intermediate, and particularly provides a preparation method of difluoropipercycline, the synthesis process of which is as follows: using a microchannel reactor, the piperonine solution is continuously and evenly pumped into module A for precooling; at the same time, the The mixed gas of fluorine gas is continuously and evenly pumped into module B for precooling; it is mixed and reacted in modules C, D, E and F in sequence, the reaction temperature is controlled at -40°C-20°C, and the product is collected at a retention time of 5s-10min; the product After washing with water and rectification, separation and purification, difluoropiperone was obtained. The method for preparing difluoropiperone has the advantages of high atom economy, rapid reaction, low cost, little pollution, environmental protection and safety.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a microchannel fluorination reaction, in particular to a microchannel fluorination synthesis technology of difluoropiperone ring. Background technique [0002] Difluoropiperone (full name: 2,2-difluoro-1,3-benzodioxol, compound 1) is a colorless liquid with a boiling point of 129°C-130°C, and is the key to the synthesis of the agricultural fungicide fluroxynil intermediate. Yan Xiaomin et al. ("World Pesticides", 2010, 32(3), 36-38) introduced the synthesis method of fludioxonil. Among them, the commonly used synthesis method of difluoropiperonyl is the fluorine-chlorine exchange method. As shown in the following reaction formula, piperonyl ring (compound 2) is first chlorinated to generate dichloro piperonyl ring (compound 3), and then fluorinated to generate difluoro piperonyl ring. The fluorine-chlorine exchange method is a classic method for fluorine atoms on compou...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D317/46
CPCC07D317/46
Inventor 张建功毛明珍王威宁斌科陈涛王列平王伦王海洋
Owner XIAN MODERN CHEM RES INST
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