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Preparation method of topramezone

A technology of fenfentrazone and phenyl, which is applied in the field of preparation of fenflumezone, can solve the problems of high production cost consumption, difficult palladium catalyst recovery, high cost, etc., and achieve low cost, short reaction time and high yield Effect

Active Publication Date: 2021-09-17
XI AN JIAOTONG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Due to the use of expensive palladium-based catalysts in the patented route developed by BASF, its cost is extremely high, and the recovery of palladium catalysts is difficult, resulting in high production costs in the large-scale production process

Method used

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  • Preparation method of topramezone
  • Preparation method of topramezone
  • Preparation method of topramezone

Examples

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Embodiment 1

[0032] A preparation method of fenflumezone, comprising the following steps:

[0033] 20g (62.8mmol) of compound I (3-[3-bromo-2-methyl-6-(methylthio)-phenyl]-4,5-dihydroisoxazole) and compound II (1-methyl Base-5-hydroxypyrazole) 6.78g (69.0mmol) is completely dissolved in 1,4-dioxane, adding catalyst cuprous chloride 0.314g (3.14mmol), ligand 1,3-bis(2, 1.218g (3.14mmol) of 6-diisopropylphenyl) imidazol-2-ylidene, 15.9g (0.157mol) of triethylamine, 25barCO to replace the air in the reactor three times, each replacement time is 10min, 3 replacements After completion, react at 100°C for 18 hours; naturally cool to room temperature after the reaction, use a vacuum rotary evaporator to remove triethylamine and 1,4-dioxane from the obtained reaction mixture, and then add 1.2% NaOH The solution is adjusted to pH=12, the insolubles in the solution are filtered out by suction filtration, the filtrate is extracted once with dichloromethane, the water layer is separated, the organic ...

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Abstract

The invention relates to a preparation method of topramezone. The method comprises: carrying out reaction on a compound I (3-[3-bromo-2-methyl-6-(methylthio)-phenyl]-4, 5-dihydroisoxazole) and a compound II (1-methyl-5-hydroxypyrazole) in the atmosphere of a copper catalyst, a ligand, an organic solvent, an alkali and a CO gas to prepare the topramezone, wherein the reaction temperature is controlled to be 25-120 DEG C, and the reaction time is 18-24 hours. The preparation method is simple and convenient to operate, the catalyst is cheap, the production cost is greatly reduced, the product yield is high, and the preparation method can be used for industrial production of topramezone.

Description

technical field [0001] The invention relates to the technical field of chemistry and chemical engineering, in particular to a preparation method of fenflumezone based on a carbon monoxide intercalation method. Background technique [0002] Topramezon (Topramezon) is a benzoyl pyrazolone herbicide developed by BASF in Germany. This compound belongs to the triketone post-emergence stem and leaf treatment agent. Phenylpyruvate dioxygenase (4-HPPD), indirectly affects the synthesis of carotenoids, thereby interfering with the synthesis and function of chlorophyll, eventually leading to severe albinism. These compounds have good weed control effects and can effectively control the main grass and broadleaf weeds on corn crops worldwide. Benfentrazone has the advantages of broad herbicidal spectrum, high activity, strong miscibility, low dosage, and safety to corn and post-stem crops. It is a relatively safe herbicide. At present, how to efficiently synthesize such compounds is a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/10B01J31/22
CPCC07D413/10B01J31/2273B01J2531/16B01J2231/4205Y02P20/584
Inventor 高品陶靖齐郭丽娜龚伟王永昌
Owner XI AN JIAOTONG UNIV