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Method for preparing halogenated biphenyl

A technology of halogenated aniline and biphenyl, which is applied in the field of preparation of halogenated biphenyl, can solve problems such as low yield of target product, difficulty in separation and purification, and easy disproportionation reaction, so as to improve equipment production capacity and shorten production cycle , The effect of increasing product yield

Inactive Publication Date: 2009-10-07
江西省化学工业研究所 +1
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  • Summary
  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

2,4-Difluorobiphenyl is an important intermediate used in the synthesis of the anti-inflammatory analgesic drug diflunisal (diflunisal), which is a new type of salicylic non-steroidal antibacterial Inflammatory, antipyretic, analgesic; 4-bromo-2-fluorobiphenyl is an important intermediate for the synthesis of anti-inflammatory analgesic flurbiprofen, which is a non-steroidal anti-inflammatory, antipyretic , analgesic; the synthetic method of halogenated biphenyl is to utilize Gomberg-Bachmann coupling reaction, and this method has more advantages, and traditional Gomberg-Bachmann reaction is carried out under neutral or alkaline condition, is free radical The reaction mechanism is prone to disproportionation reaction, resulting in low yield of the target product, and separation and purification are very difficult, but the low yield is the biggest problem encountered in industrial production, and the highest yield in foreign literature is only 52.5%. , Domestic Shaanxi Chemical Industry Magazine, 1999, 28 (2): 21-22, 29 "2,4-Difluorobiphenyl Synthesis New Technology" has also done research on this reaction, and the crude product yield reached 85.8%; Hangzhou Chemical Industry Magazine 2003

Method used

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  • Method for preparing halogenated biphenyl
  • Method for preparing halogenated biphenyl
  • Method for preparing halogenated biphenyl

Examples

Experimental program
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Effect test

Embodiment 1

[0023] 1. Make a self-made copper-containing composite catalyst, add dimethylformamide into the reactor, fill with nitrogen for protection, then add 0.1 equivalent of ammonium formate and 0.5 equivalent of N, N, N', N'-tetraphenylethylenediamine and 0.1 equivalent of CuCl 2 and 0.01 equivalent of PdCl 2 , and then the mixture was heated to 30 ° C, fully stirred and maintained for 15 hours, cooled, filtered, and vacuum-dried.

[0024] 2. Add 100KG trichloroacetic acid, 5KG anhydrous magnesium sulfate, 1KG self-made copper-containing composite catalyst, 1000L benzene, and 50KG 2,4-difluoroaniline into the synthesis kettle, start stirring, open the jacket to cool the brine, slowly Slowly cool down to 10-20°C. Add isopropyl nitrite dropwise, and control the reaction temperature at 10-20°C. After the reaction is completed, use compressed air to hydraulically press the synthesis kettle to wash the kettle, add 200L of water each time, stir for 15-30 minutes, and wash for 3 times. ...

Embodiment 2

[0026] 1. Make a self-made copper-containing composite catalyst, add dimethylformamide into the reactor, fill with nitrogen for protection, then add 0.5 equivalent of ammonium formate and 0.8 equivalent of N, N, N', N'-tetraphenylethylenediamine and 0.2 equivalents of CuCl 2 and 0.02 equivalent of PdCl 2 , and then the mixture was heated to 45 ° C, fully stirred and maintained for 20 hours, cooled, filtered, and vacuum-dried.

[0027] 2. Add 150KG trichloroacetic acid, 8KG anhydrous magnesium sulfate, 1.5KG self-made copper-containing composite catalyst, 1500L benzene, and 80KG 2,4-difluoroaniline into the synthesis kettle, start stirring, open the jacket to cool the brine, Slowly cool down to 10-20°C. Add isopropyl nitrite dropwise, and control the reaction temperature at 10-20°C. After the reaction is completed, use compressed air to hydraulically press the synthesis kettle to wash the kettle, add 350L of water each time, stir for 15-30 minutes, wash 3 times, discharge th...

Embodiment 3

[0029] 1. Make a self-made copper-containing composite catalyst, add dimethylformamide into the reactor, fill with nitrogen for protection, then add 1.0 equivalent of ammonium formate and 1.0 equivalent of N, N, N', N'-tetraphenylethylenediamine and 0.3 equivalents of CuCl 2 and 0.03 equivalent of PdCl 2 , and then heat the mixture to 60°C, keep it fully stirred for 24 hours, cool, filter, and vacuum dry to obtain the final product;

[0030] 2. Add 200KG trichloroacetic acid, 10KG anhydrous magnesium sulfate, 2KG self-made copper-containing composite catalyst, 1500L benzene, and 100KG 2,4-difluoroaniline into the synthesis kettle, start stirring, open the jacket to cool the brine, and slowly Cool down to 10-20°C. Add isopropyl nitrite dropwise, and control the reaction temperature at 10-20°C. After the reaction is completed, use compressed air to hydraulically press the synthesis kettle to wash the kettle, add 500L of water each time, stir for 15-30 minutes, and wash 3 time...

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Abstract

The present invention relates to a method for synthesizing halogenated biphenyl, wherein one halogenated aniline of 4-bromium-2-fluoroaniline or 2, 4-difluoro aniline or 2-fluoroaniline or 4-fluoroaniline or the like, and the benzene are used as the principal raw material under a acidic condition, the trichloroacetic acid, the anhydrous magnesium sulphate and homemade composite catalyst containing copper or zinc or iron are added into a same reactor, and a diazotization reaction and a coupling reaction are completed synchronously. The invention also discloses a method for preparing a homemade composite catalyst containing a metal, including the steps: adding the dimethylformamide into a reactor, filling the nitrogen to protect, adding 0.1-1.0 equivalent weight ammonium formate, 0.5-1.0 equivalent weight N, N, N', N'-tetraphenyl ethylene diamine and 0.1-0.3 equivalent weight CuCl2 or ZnCl2 or FeCl3 and 0.01-0.03 equivalent weight PdCl2, then mixing and heating until 30-60 DEG C, agitating thoroughly and holding for 15-24 hours, cooling, filtrating and vacuum drying, the composite catalyst containing a metal will be obtained. By means of using a same reactor, the halogenated biphenyl may be prepared by the diazotization and the coupling reaction completed in one same step, the yield is more than 85% by the halogenated aniline. The product content achieves 99.5%, the production period is shortened greatly, the equipment production capacity is improved, the energy consumption and material consumption are all reduced, and the work intensity of workers is alleviated greatly, thus the method of the invention is very suitable for an industrialization great production.

Description

technical field [0001] The invention relates to a preparation method of halogenated biphenyl, in particular to a preparation method of 2,4-difluorobiphenyl and 4-bromo-2-fluorobiphenyl. Background technique [0002] Halogenated biphenyl products include 2,4-difluorobiphenyl, 4-bromo-2-fluorobiphenyl, 2-fluorobiphenyl, 4-fluorobiphenyl, 2-bromobiphenyl, 4-bromobiphenyl and other halogenated Biphenyls. 2,4-Difluorobiphenyl is an important intermediate used in the synthesis of the anti-inflammatory analgesic drug diflunisal (diflunisal), which is a new type of salicylic non-steroidal antibacterial Inflammatory, antipyretic, analgesic; 4-bromo-2-fluorobiphenyl is an important intermediate for the synthesis of anti-inflammatory analgesic flurbiprofen, which is a non-steroidal anti-inflammatory, antipyretic , analgesic; the synthetic method of halogenated biphenyl is to utilize Gomberg-Bachmann coupling reaction, and this method has more advantages, and traditional Gomberg-Bachm...

Claims

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Application Information

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IPC IPC(8): C07C17/263C07C25/18B01J23/89B01J23/60
Inventor 宋建平徐正安蔡汉兴巫民建宋夏辉胡云根朱明生辜高龙张沛方卫红李红廖爱平
Owner 江西省化学工业研究所
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