Synthesis method of 2-(difluoromethyl)pyridine-3-ol

A kind of technology of difluoromethyl group and synthetic method is applied in the field of synthesis of 2-pyridine-3-ol, can solve the problems such as the complete route of 2-(difluoromethyl)pyridine-3-ol which is not reported in the literature, etc., and achieves synthesis Simple operation, short process route, easy to achieve effect

Active Publication Date: 2020-04-10
阿里生物新材料(常州)有限公司
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

Mainly solve the technical problem that there is no complete route for the synthesis of 2-(difluoromethyl)pyridin-3-ol reported in the literature

Method used

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  • Synthesis method of 2-(difluoromethyl)pyridine-3-ol

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Experimental program
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Effect test

Embodiment 1

[0025] 3-Methoxypyridine-2-carbaldehyde (24.7g, 180mmol, 1eq.) was dissolved in 480ml of dichloromethane, and cooled to -78°C. Under nitrogen protection, diethylaminosulfur trifluoride (87g, 540mmol, 3eq.) was added dropwise. After the dropwise addition, the reaction was carried out at 25° C. for 15 hours.

[0026] After the reaction, the reaction solution was dropped into ice water and adjusted to alkalinity with saturated sodium bicarbonate solution. After extraction with ethyl acetate, the organic phase was concentrated and subjected to column chromatography to obtain 26.1 g of oily 2-(difluoromethyl)-3-methoxypyridine, with a yield of 91%. used directly in the next reaction.

[0027] Take 95ml of acetic acid and cool it. 190ml mass fraction of 37% hydrobromic acid was added dropwise to the acetic acid and mixed. Then the above mixed acid was added dropwise into the reaction flask of 2-(difluoromethyl)-3-methoxypyridine, the temperature was raised to 115° C., and the re...

Embodiment 2

[0031] 3-Methoxypyridine-2-carbaldehyde (20.6g, 150mmol, 1eq.) was dissolved in 400ml of dichloromethane, and cooled to -78°C. Under nitrogen protection, diethylaminosulfur trifluoride (72.5 g, 450 mmol, 3 eq.) was added dropwise. After the dropwise addition, the reaction was carried out at 5° C. for 30 hours.

[0032] After the reaction, the reaction solution was dropped into ice water and adjusted to alkalinity with saturated sodium bicarbonate solution. After extraction with ethyl acetate, the organic phase was concentrated and subjected to column chromatography to obtain 19.6 g of oily 2-(difluoromethyl)-3-methoxypyridine with a yield of 82%. used directly in the next reaction.

[0033] Take 70ml of acetic acid and cool it. 140ml mass fraction of 37% hydrobromic acid was added dropwise to the above-mentioned acetic acid, and mixed. Then, the above mixed acid was added dropwise into the reaction flask of 2-(difluoromethyl)-3-methoxypyridine, the temperature was raised t...

Embodiment 3

[0037] 3-Methoxypyridine-2-carbaldehyde (27.4g, 200mmol, 1eq.) was dissolved in 520ml of dichloromethane and cooled to -78°C. Under nitrogen protection, diethylaminosulfur trifluoride (96.7g, 600mmol, 3eq.) was added dropwise. After the dropwise addition, the reaction was carried out at 40° C. for 3 hours.

[0038] After the reaction, the reaction solution was dropped into ice water and adjusted to alkalinity with saturated sodium bicarbonate solution. After extraction with ethyl acetate, the organic phase was concentrated and subjected to column chromatography to obtain 23.9 g of oily 2-(difluoromethyl)-3-methoxypyridine, with a yield of 75%. used directly in the next reaction.

[0039] Take 85ml of acetic acid and cool it. 170ml mass fraction of 37% hydrobromic acid was added dropwise to the acetic acid and mixed. Then the above mixed acid was added dropwise into the reaction flask of 2-(difluoromethyl)-3-methoxypyridine, the temperature was raised to 80° C., and the rea...

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Abstract

The invention discloses a synthesis method of 2-(difluoromethyl)pyridine-3-ol, and belongs to the field of organic chemical synthesis. The method comprises the following steps: dissolving 3-methoxypyridine-2-formaldehyde into an organic solvent, and performing reaction with diethylamino sulfur trifluoride under the protection of nitrogen to obtain 2-(difluoromethyl)-3-methoxypyridine; and reactingthe 2-(difluoromethyl)-3-methoxypyridine with an acid to obtain the target product 2-(difluoromethyl)pyridine-3-ol. The method is reasonable in process design, short in route, simple in synthesis operation and easy to implement.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a synthesis method of 2-(difluoromethyl)pyridin-3-ol. Background technique [0002] Pyridine compounds are important fine chemical raw materials, synthetic raw materials and intermediates of many chemicals such as drugs and materials, and also important constituent units of catalyst ligands in organic synthesis. The introduction of fluorine atoms into the molecule can improve the biological activity and performance of the compound, making it have the advantages of less dosage, low toxicity, high efficacy, and strong metabolism. At present, a variety of fluorine-containing pyridine compounds have been applied in the fields of pesticides and medicines. For example, fluazinam as a fungicide has the characteristics of high efficiency, low toxicity, and broad spectrum. It also has insecticidal activity and can kill mosquitoes and flies, but it is safe for humans, livestock, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/65
CPCC07D213/65
Inventor 史建云刘超戴红升徐向成顾云龙
Owner 阿里生物新材料(常州)有限公司
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