Synthetic method of 3, 5-dichloro-2, 4-difluoroaniline

A technology of difluoroaniline and synthesis method, which is applied in chemical instruments and methods, preparation of amino compounds, preparation of organic compounds, etc., can solve the problems of high cost, three wastes, and difficult availability of raw materials, and achieve low cost and avoid isomers , The effect of reducing the pollution of three wastes

Active Publication Date: 2012-08-01
江西吉翔医药化工有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] In order to overcome the disadvantages of unavailable raw materials, high cost, and serious wastes in the prior art, the present invention provides a new low-cost synthesis method of 3,5-chloro-2,4-difluoroaniline

Method used

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  • Synthetic method of 3, 5-dichloro-2, 4-difluoroaniline
  • Synthetic method of 3, 5-dichloro-2, 4-difluoroaniline

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Take 43.0 g of the distillation residue of the production process of 2,4-dichloro-3-fluoronitrobenzene (from an enterprise in Kaihua, Zhejiang Province to prepare 2,4-dichloro-3-fluoronitrobenzene by nitration of 2,6-dichlorofluorobenzene Distillation residue with batch number 20110912 in 2011 production process of benzene, in which 3,5-dichloro-4-fluoronitrobenzene content is 83.7%, 2,4-dichloro-3-fluoronitrobenzene content is 14.6%) and Dissolve 2.0 g of iodine in 80 mL of DMSO, raise the temperature to 140 °C and start flowing chlorine gas, react for 12 h, stop the chlorine flow, pour the reaction solution into ice water, wash the organic phase with NaOH aqueous solution until neutral to obtain 2,3,5-tris Chloro-4-fluoronitrobenzene, yield 89%.

[0027] 24.5 g (0.1 mol) of 2,3,5-trichloro-4-fluoronitrobenzene, 11.7 g (0.2 mol) of anhydrous potassium fluoride, and 2 g of tetrabutylammonium bromide in 60 mL of sulfolane at 160 °C After reacting for 12 h, 19.5 g of 2,4...

Embodiment 2

[0030] Take 43.5 g of the distillation residue of 2,4-dichloro-3-fluoronitrobenzene production process (from an enterprise in Quzhou, Zhejiang Province to prepare 2,4-dichloro-3-fluoronitrobenzene by nitration of 2,6-dichlorofluorobenzene Distillation residue with batch number HJ110837 in the benzene production process in 2011, of which 3,5-dichloro-4-fluoronitrobenzene content is 85.5%, 2,4-dichloro-3-fluoronitrobenzene content is 11.3%), Stir 1.5 g of iron powder and 60 mL of concentrated sulfuric acid to raise the temperature to 150 °C, start chlorine gas flow, react for 8 h, stop chlorine flow, cool down, pour the reaction solution into ice water, wash the organic phase with NaOH aqueous solution until neutral to obtain 2,3, 5-trichloro-4-fluoronitrobenzene, yield 86.5%.

[0031] 24.5 g (0.1 mol) of 2,3,5-trichloro-4-fluoronitrobenzene, 11.7 g (0.2 mol) of anhydrous potassium fluoride, and 60 mL of tetramethylurea were reacted at 180 °C for 10 h, and distilled under reduce...

Embodiment 3

[0034] Take 44.0 g of the distillation residue of the production process of 2,4-dichloro-3-fluoronitrobenzene (from an enterprise in Linhai, Zhejiang to prepare 2,4-dichloro-3-fluoronitrobenzene by nitration of 2,6-dichlorofluorobenzene Distillation residue with batch number YT20110622 in the benzene production process in 2011, in which 3,5-dichloro-4-fluoronitrobenzene content is 80.9%, 2,4-dichloro-3-fluoronitrobenzene content is 14.3%) and 80 mL of chlorosulfonic acid was warmed up to 120 °C and started to pass chlorine gas, reacted for 10 h, stopped the chlorine flow, poured the reaction solution into a large amount of ice water, let it stand, and filtered to obtain 2,3,5-trichloro-4-fluoronitrobenzene, The yield is 90%.

[0035] 24.5 g (0.1 mol) of 2,3,5-trichloro-4-fluoronitrobenzene, 11.7 g (0.2 mol) of anhydrous potassium fluoride, 2 g of polyethylene glycol-6000 and 60 mL of benzonitrile were heated to Reacted at 150 °C for 12 h, and distilled under reduced pressure ...

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Abstract

The invention discloses a synthetic method of 3, 5-dichloro-2, 4-difluoroaniline. The synthetic method takes distillation residues which are generated in the manufacturing technology that 2,6-dichlor fluorbenzene is nitrified to prepare 2, 4-dichloro-3-fluoronitrobenzene as raw material, and the distillation residues are chlorinated through chlorine gas and fluorated through potassium fluoride so as to prepare 3, 5-dichloro-2, 4-difluoro nitrobenzene; and finally, 3, 5-dichloro-2, 4-difluoro nitrobenzene is reduced to obtain 3, 5-dichloro-2, 4-difluoroaniline. The synthetic method adopts by-products that are generated in the conventional manufacturing technology line as raw material, is directly used for synthesizing 3, 5-dichloro-2, 4-difluoroaniline without any treatment, is characterized by low price of raw material, full resource utilization, mild reaction conditions, high yield coefficient of products, low manufacturing cost and the like compared with a conventional method for preparing 3,5-dichloro-2,4-difluoroaniline, is easy to get raw material, and is very suitable for industrialized production.

Description

technical field [0001] The invention relates to a new method for synthesizing the intermediate 3,5-dichloro-2,4-difluoroaniline of the insecticide chlorfenuron. Background technique [0002] 3,5-dichloro-2,4-difluoroaniline is an important intermediate in the synthesis of benzoylurea insecticide teflubenzuron. [0003] Fufenuron is a benzoylurea insecticide first developed and marketed by Celamerck GmbH & Co. in 1984, and it has been registered for use in many countries in the world. It achieves the purpose of killing pests by inhibiting the synthesis of chitin in the epidermis of insects. Its unique mechanism of action makes it less toxic to humans, animals, and insect natural enemies. It has become an important new generation of insecticides with high efficiency and low toxicity. Insecticide. It still has a good control effect on pests that have developed resistance to organophosphates, pyrethroids, carbamates and other insecticides. [0004] [0005] [0006] Regar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/52C07C209/36
Inventor 郑士才聂孝文况庆雷郑建霖魏源陈锋王吉
Owner 江西吉翔医药化工有限公司
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