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Synthesis method of diphenyl ether derivate, combined production method of oxyfluorfen and acifluorfen and synthesis method of oxyfluorfen

A synthesis method and derivative technology, applied in chemical instruments and methods, preparation of organic compounds, preparation of sulfonamides, etc., can solve the problems of high environmental protection pressure, high comprehensive cost, low comprehensive cost, etc., and achieve high product content , reduced production costs, high process safety and economical effects

Active Publication Date: 2011-04-27
SHANGYU NUTRICHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0028] The purpose of the present invention is to overcome the problems of low raw material utilization rate, high environmental protection pressure and high comprehensive cost of the existing double etherification route for producing oxyfluorfen Defects, provide a new synthesis method of diphenyl ether derivatives with high raw material utilization rate, low overall cost and environmental protection

Method used

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  • Synthesis method of diphenyl ether derivate, combined production method of oxyfluorfen and acifluorfen and synthesis method of oxyfluorfen
  • Synthesis method of diphenyl ether derivate, combined production method of oxyfluorfen and acifluorfen and synthesis method of oxyfluorfen
  • Synthesis method of diphenyl ether derivate, combined production method of oxyfluorfen and acifluorfen and synthesis method of oxyfluorfen

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preparation example Construction

[0063] It is characterized in that the synthesis method comprises: in the first organic medium, contacting 3-chloro-4-hydroxytrifluorotoluene, that is, the compound of formula (2) with the compound of formula (3) under the first contact condition;

[0064]

[0065] Formula (2) Formula (3)

[0066] In formula (3), R 2 'is -H, -Cl, -COOH, -CONHSO 2 CH 3 、-OC 2 h 5 、-COOCH 2 COOC 2 h 5 , -COOCH(CH 3 )COOC 2 h 5 ,with One of the R 3 ’ for -NO 2 or -Cl;

[0067] The first organic medium is one or more of dichloromethane, dichloroethane, tetrachloroethylene, dimethylformamide, dimethylacetamide and dimethyl sulfoxide.

[0068] According to the present invention, the condensation reaction conditions may include: the contact temperature may be 40-160°C, preferably 40-80°C, and the contact time may be 2-30 hours, preferably 2-10 hours.

[0069] According to the present invention, relative to 1 mole of the compound of formula (2), the amount of the compound of for...

Embodiment approach

[0091] According to a preferred embodiment of the present invention, the preparation method of the 3-chloro-4-hydroxytrifluorotoluene, that is, the compound of formula (2), comprises: in the fourth organic medium, the compound of formula (4) is contacting with alkali and ethanol under ether exchange reaction conditions; and separating oxyfluorfen in the product obtained after contacting, and acidifying the separated product;

[0092]

[0093] Formula (4);

[0094] Wherein, the ether exchange reaction conditions may include: the contact temperature may be 0-80°C, preferably 20-50°C, the contact time may be 1-20 hours, preferably 5-10 hours; relative to 1 mole of the formula ( 4) compound, the consumption of alkali can be 1-4 mole, preferably 2-3 mole; The consumption of ethanol can be 1-10 mole, is preferably 1-5 mole, and the consumption of the 4th organic medium can be 1-10 liters, preferably 1-5 liters; the fourth organic medium is triethylamine and / or pyridine; the alka...

preparation Embodiment 1

[0125] This preparation example produces oxyfluorfen through the double etherification route, and produces 3-chloro-4-hydroxytrifluorotoluene.

[0126] In a 2000ml three-necked flask, add 55g resorcinol (0.50mol), 67.2g potassium hydroxide, 420g toluene, and 500g DMSO, stir and control the temperature between 115-125°C, keep it for 120 minutes and then cool to 70-75°C, evaporate the toluene under reduced pressure, then cool to 60-65°C, add 193.5g of 3,4-dichlorobenzotrifluoride, 4.2g of copper oxide, heat up to 140-145°C, and keep it for 12 hours , DMSO was removed by evaporation under reduced pressure, then 500g of toluene was added, the reaction solution in the there-necked flask was filtered, and the filtrate was washed with alkali solution (the alkali solution was an aqueous sodium hydroxide solution with a concentration of 10% by weight) twice (each 10mL alkali solution) Thereafter, toluene was removed by evaporation under reduced pressure. After adding 550g of 1,2-dichl...

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Abstract

The invention provides a synthesis method of a diphenyl ether derivate. The diphenyl ether derivate has a structure as shown in formula (1). The synthesis method comprises the following step: enabling 3-chloro-4-hydroxyl benzotrifluoride (a compound as shown in formula (2)) to be in contact with a compound as shown in formula (3). By using the 3-chloro-4-hydroxyl benzotrifluoride as the starting material to synthesize the diphenyl ether derivate, the synthesis method can realize the reutilization of byproducts (3-chloro-4-hydroxyl benzotrifluoride) in the dual-etherification process route foroxyfluorfen production. Besides, by using the 3-chloro-4-hydroxyl benzotrifluoride to synthesize diphenyl ether herbicides, the content of the product can be increased to more than 90%.

Description

technical field [0001] The invention relates to a method for synthesizing diphenyl ether derivatives, a co-production method for oxyfluorfen and acifluorfen, and a method for synthesizing oxyfluorfen. Background technique [0002] Protoporphyrinogen oxidase (PPO) is a key enzyme in chlorophyll biosynthesis and a molecular target of peroxidative herbicides. After treating plants with herbicides such as diphenyl ethers, phthalimides, and some pyridine derivatives, the activity of protoporphyrinogen oxidase will be inhibited, resulting in the accumulation of protoporphyrinogen IX, and the accumulated protoporphyrinogen IX Under light, it can destroy the photosynthetic electron transport system and oxidize the thylakoid membrane, eventually leading to plant death. [0003] The herbicide whose action target is protoporphyrinogen oxidase has excellent characteristics such as low dosage, high activity, wide herbicidal spectrum, low toxicity to mammals, and less impact on the envir...

Claims

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Application Information

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IPC IPC(8): C07C205/38C07C205/59C07C201/12C07C39/26C07C37/055C07C311/51C07C303/40
Inventor 游华南冯应江高庆林徐金鹏胡万全杜晓华王榕
Owner SHANGYU NUTRICHEM
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