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Synthesis method of pinoxaden

A technology of pinoxaden and its synthetic method, which is applied in the field of pinoxaden synthesis, can solve the problems of high cost, long reaction steps, cumbersome operation, etc., and achieve the effects of simple operation, less environmental pollution, and high economic efficiency

Active Publication Date: 2018-11-23
兰州精细化工有限责任公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of this invention is to provide a kind of synthetic method of pinoxaden, to solve the problem of high cost caused by long reaction steps and cumbersome operation in the existing method

Method used

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  • Synthesis method of pinoxaden

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Experimental program
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Effect test

Embodiment 1

[0029] (1), the synthesis of 2,6-diethyl-4-methylbromobenzene

[0030] Hydrogen bromide adds in twice in the following steps,

[0031] First in an ice bath, dissolve 2,6-diethyl-4-methylaniline (12 g, 73.5 mmol) in hydrobromic acid (40%, 14.9 mL, first addition), and ethanol (90 mL) Add them together into the reaction flask, and then add a solution of sodium nitrite (5.58 g, 80.9 mmol) in water (6 mL) dropwise to the solution obtained above. Then the above solution was added to the solution of cuprous bromide (2.11g, 14.7mmol) in hydrobromic acid (40%, 68.9mL, added for the second time), and the temperature was raised to 80°C, and the reaction was kept for 3h, and the reaction was detected by TLC. . Then the reaction solution was cooled to room temperature, diluted with water (50 mL), extracted three times with ethyl acetate (100 mL), the organic layer was collected, washed once with sodium bicarbonate solution, dried over magnesium sulfate, and the solvent was distilled off...

Embodiment 2

[0039] (1), the synthesis of 2,6-diethyl-4-methylbromobenzene

[0040] In an ice bath, 2,6-diethyl-4-methylaniline (12g, 73.5mmol) was dissolved in hydrobromic acid (40%, 24.1mL), and ethanol (90mL) was added to the reaction flask together, A solution of sodium nitrite (6.8 g, 98.5 mmol) in water (6 mL) was then added dropwise to the above obtained solution. Then the solution obtained above was added to a solution of cuprous bromide (6.2g, 44.1mmol) in hydrobromic acid (40%, 121.3mL), the temperature was raised to 95°C, and the reaction was incubated for 2 hours. TLC detected that the reaction was complete. Then the reaction solution was cooled to room temperature, diluted with water (50 mL), extracted three times with ethyl acetate (100 mL), the organic layer was collected, washed once with sodium bicarbonate solution, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was purified by column chr...

Embodiment 3

[0048] (1), the synthesis of 2,6-diethyl-4-methylbromobenzene

[0049] In an ice bath, 2,6-diethyl-4-methylaniline (12g, 73.5mmol) was dissolved in hydrobromic acid (40%, 27.9mL), and ethanol (90mL) was added to the reaction flask together, A solution of sodium nitrite (7.61 g, 110.25 mmol) in water (6 mL) was then added dropwise to the above obtained solution. Then the solution obtained above was added to a solution of cuprous bromide (8.4g, 58.8mmol) in hydrobromic acid (40%, 140.7mL), heated to 80°C, kept for 2 hours, and TLC detected that the reaction was complete. Then the reaction solution was cooled to room temperature, diluted with water (50 mL), extracted three times with ethyl acetate (100 mL), the organic layer was collected, washed once with sodium bicarbonate solution, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (petroleum ether) to obtain...

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Abstract

The invention discloses a synthesis method of pinoxaden, and belongs to the field of chemical engineering. The method comprises the following steps that 2,6-diethyl-4-methylaniline is subjected to sodium nitrite diazotization and thermal decomposition to generate 2,6-diethyl-4-methylbromobenzene; diethyl malonate is added into [1,4,5]-oxadiazepine dihydrobromide hydrate and an alkaline catalyst tosynthesize dihydro-1H-pyrazolo[1,2-d][1,4,5]-oxadiaza-7,9(2H, 8H)-diketone, the dihydro-1H-pyrazolo[1,2-d][1,4,5]-oxadiaza-7,9(2H, 8H)-diketone and 2,6-diethyl-4-bromomethyl benzene are subjected tocoupling reaction to obtain 8-(2,6-diethyl-4-methyl phenyl)tetrahydropyrazolo[1,2-d][1,4,5]xazepine-7, 9(2H, 8H)-diketone; the 8-(2,6-diethyl-4-methyl phenyl)tetrahydropyrazolo[1,2-d][1,4,5]xazepine-7, 9(2H, 8H)-diketone is reacted with pivaloyl chloride to synthesize the final product pinoxaden. According to the synthesis method of the pinoxaden, the synthesis steps are shortened, operation is simple and convenient, the cost is reduced, the economic efficiency is high, and environmental pollution is little.

Description

technical field [0001] The invention belongs to the field of chemical industry, in particular to a method for synthesizing pinoxaden. Background technique [0002] Pinoxaden is a new phenylpyrazole herbicide with excellent herbicidal activity. Because of its advantages of high efficiency, broad spectrum and high safety, it has been widely used in the field of pesticides, especially in the field of herbicides in wheat fields. Its synthesis is one of the research hotspots in the field of pesticides in recent years. To study the synthesis of pinoxaden, the key is to study the synthesis of intermediate 2-(2,6-diethyl-4-methylphenyl)malonic acid derivatives. In the existing method, 2,6 The synthesis of 2-(2,6-diethyl-4-methylphenyl)malonic acid derivatives with -diethyl-4-methylaniline as the starting material is the most suitable method for industrial production needs. The traditional method of synthesizing pinoxaden with 2,6-diethyl-4-methylaniline as starting material is as...

Claims

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Application Information

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IPC IPC(8): C07D498/04
CPCC07D498/04
Inventor 刘荣王晓霞姬鹏燕魏万磊何开宇刘云利
Owner 兰州精细化工有限责任公司
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