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Preparation method of 4-bromo-6-chloropyridine-2-carboxylic acid

A technology of chloropyridine and carboxylic acid, which is applied in the field of compound synthesis, can solve the problems of unpublished 4-bromo-6-chloropyridine-2-carboxylic acid synthesis method, etc., and achieve the effect of cheap raw materials, easy to obtain raw materials, and simple operation

Active Publication Date: 2020-12-08
郑州猫眼农业科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthetic method of 4-bromo-6-chloropyridine-2-carboxylic acid is not disclosed in the prior art

Method used

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  • Preparation method of 4-bromo-6-chloropyridine-2-carboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The preparation method of the 4-bromo-6-chloropyridine-2-carboxylic acid of the present embodiment comprises the following steps:

[0023] 1) Take a dry 100mL three-necked flask, add 12.5g of compound 1 and 50mL of DMF to it, compound 1 is 2,4-dihydroxy-6-picoline, put the three-necked flask in an ice-water bath, add 22.1g of phosphorus oxybromide, and then put the three-necked flask in an oil bath at 110°C, stir for 1 hour, and cool to 30°C. After cooling, add 60mL of water to the three-necked flask, then adjust the pH to 7 with sodium carbonate, precipitate a large amount of solid, filter, wash the filter cake once with 10mL of cold ethanol, wash once with 10mL of ether, and drain to obtain the compound 2 is 11.3g, the yield is 78%. Compound 2 is 2-hydroxy-4-bromo-6-methylpyridine.

[0024] 2) Take a dry 100mL three-necked bottle, add 5.64g of compound 2 and 30mL of DMF to it, place the three-necked bottle in an ice-water bath, add 7.7g of phosphorus oxychloride, and...

Embodiment 2

[0029] The preparation method of the 4-bromo-6-chloropyridine-2-carboxylic acid of the present embodiment comprises the following steps:

[0030] 1) Take a dry 100mL three-necked flask, add 12.5g of compound 1 and 50mL of DMF to it, compound 1 is 2,4-dihydroxy-6-picoline, put the three-necked flask in an ice-water bath, add 14.3g of phosphorus oxybromide, and then the three-necked flask was placed in an oil bath at 110°C, stirred for 1 hour, and cooled to 28°C. After cooling, add 60mL of water to the three-necked flask, then adjust the pH to 7 with sodium carbonate, precipitate a large amount of solid, filter, wash the filter cake once with 10mL of cold ethanol, wash once with 10mL of ether, and drain to obtain the compound 2 was 5.7 g, and the yield was 61%. Compound 2 was 2-hydroxy-4-bromo-6-methylpyridine.

[0031] 2) Take a dry 100mL three-necked bottle, add 5.64g of compound 2 and 30mL of DMF to it, place the three-necked bottle in an ice-water bath, add 15.4g of phospho...

Embodiment 3

[0034] The preparation method of the 4-bromo-6-chloropyridine-2-carboxylic acid of the present embodiment comprises the following steps:

[0035] 1) Take a dry 100mL three-necked flask, add 12.5g of compound 1 and 50mL of DMF to it, compound 1 is 2,4-dihydroxy-6-picoline, put the three-necked flask in an ice-water bath, add 22.1g of phosphorus oxybromide, and then put the three-necked flask in an oil bath at 110°C, stir for 1 hour, and cool to 30°C. After cooling, add 60mL of water to the three-necked flask, then adjust the pH to 7 with sodium carbonate, precipitate a large amount of solid, filter, wash the filter cake once with 10mL of cold ethanol, wash once with 10mL of ether, and drain to obtain the compound 2 is 11.3g, the yield is 78%. Compound 2 is 2-hydroxy-4-bromo-6-methylpyridine.

[0036] 2) Take a dry 100mL three-necked bottle, add 5.64g of compound 2 and 30mL of toluene to it, place the three-necked bottle in an ice-water bath, add 7.7g of phosphorus oxychloride,...

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Abstract

The invention relates to a preparation method of 4-bromo-6-chloropyridine-2-carboxylic acid. The preparation method of the 4-bromo-6-chloropyridine-2-carboxylic acid comprises the following steps: carrying out primary substitution reaction on 2,4-dihydroxy-6-methylpyridine and one of phosphorus oxybromide, phosphorus pentabromide or tetrabutylammonium bromide to generate 2-hydroxy-4-bromo-6-methylpyridine; carrying out secondary substitution reaction on the 2-hydroxy-4-bromine-6-methyl pyridine and phosphorus oxychloride or phosphorus pentachloride to generate 4-bromine-6-methyl-2-pyridine; according to the preparation method of the 4bromo 6chloropyridine 2carboxylic acid, the raw materials are cheap and easy to obtain, column chromatography purification is not needed in the reaction process, and the operation is simple and convenient.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis, and in particular relates to a preparation method of 4-bromo-6-chloropyridine-2-carboxylic acid. Background technique [0002] Pyridinecarboxylic acid is a commonly used herbicide. 4-Bromo-6-chloropyridine-2-carboxylic acid belongs to pyridine carboxylic acid, and 4-bromo-6-chloropyridine-2-carboxylic acid is also a common intermediate for synthetic medicine and materials. No synthetic method of 4-bromo-6-chloropyridine-2-carboxylic acid is disclosed in the prior art. Contents of the invention [0003] The purpose of this invention is to provide a kind of preparation method of 4-bromo-6-chloropyridine-2-carboxylic acid, the preparation method raw material of this 4-bromo-6-chloropyridine-2-carboxylic acid is cheap and easy to get, in the reaction process , without column chromatography purification, easy to operate. [0004] In order to achieve the above object, the technical sche...

Claims

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Application Information

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IPC IPC(8): C07D213/79C07D213/807C07D213/61C07D213/64
CPCC07D213/79C07D213/807C07D213/61C07D213/64
Inventor 不公告发明人
Owner 郑州猫眼农业科技有限公司
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