Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method of 4'-chloro-2-nitrobiphenyl

A technology of nitrobiphenyl and nitro, applied in the field of organic compound synthesis, can solve the problems of low yield, cumbersome operation, and many "three wastes", and achieve the effect of high yield and simple process

Active Publication Date: 2021-02-12
湖南海利常德农药化工有限公司
View PDF6 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] This method has a low yield, and many kinds of raw materials are used, the operation is cumbersome, the post-processing is difficult, there are many "three wastes", and industrial production is difficult

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of 4'-chloro-2-nitrobiphenyl
  • Preparation method of 4'-chloro-2-nitrobiphenyl
  • Preparation method of 4'-chloro-2-nitrobiphenyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] A preparation method of 4'-chloro-2-nitrobiphenyl of the present invention comprises the following steps:

[0038] Add 23.95g (99%, 0.1mol) 1-chloro-4-(6-nitrocyclohex-3-enyl)-benzene, 26.08g (0.3mol) 1%-Fe / MnO 2and 71.85g of toluene, heated to 110°C and then incubated for 4 hours. After the reaction, the reaction product was filtered, solvent removed, and methanol was added for recrystallization to obtain 19.3 g of yellow solid 4'-chloro-2-nitrobiphenyl with a content of 98.3% and a yield of 81.2%. 1 H-NMR (600MHz, CDCl 3 ): δ=7.23(s, 1H), 7.24(s, 1H), 7.39-7.42(m, 3H), 7.51(d, J=7.8Hz, 1H), 7.61(d, J=5.4Hz, 1H) , 7.87 (d, J=7.8Hz, 1H), demonstrating the successful preparation of 4'-chloro-2-nitrobiphenyl.

[0039] In the present embodiment, the preparation process of oxidizing agent is as follows:

[0040] Weigh 31.6g (0.2mol) of potassium permanganate and dissolve it in 600g of deionized water, slowly add 480g of 30% hydrogen peroxide solution dropwise under stir...

Embodiment 2

[0042] A preparation method of 4'-chloro-2-nitrobiphenyl of the present invention comprises the following steps:

[0043] 23.95g (99%, 0.1mol) 1-chloro-4-(6-nitrocyclohex-3-enyl)-benzene, 34.78g (0.4mol) 0.1%-Co / MnO 2 and 191.6g of chlorobenzene, heated to 128°C and then kept for 5h reaction. After the reaction, the reaction product was filtered, solvent removed, and methanol was added for recrystallization to obtain 19.81 g of yellow solid 4'-chloro-2-nitrobiphenyl with a content of 98.7% and a yield of 83.7%.

[0044] In the present embodiment, the preparation process of oxidizing agent is as follows:

[0045] Weigh 31.6g (0.2mol) of potassium permanganate and dissolve it in 600g of deionized water, and slowly add 480g of 30% hydrogen peroxide solution dropwise under stirring. Use nitric acid and KOH to adjust the reaction system to maintain weak alkalinity (pH=7~9), then add 10g of cobalt nitrate solution containing 0.058g (0.2mmol) dropwise, continue to react for 30min a...

Embodiment 3

[0047] A preparation method of 4'-chloro-2-nitrobiphenyl of the present invention comprises the following steps:

[0048] 23.95g (99%, 0.1mol) 1-chloro-4-(6-nitrocyclohex-3-enyl)-benzene, 17.39g (0.2mol) 5%-Ni / MnO 2 and 95.8g xylene, heated to 138°C and then kept for 6h reaction. After the reaction, the reaction product was filtered, solvent removed, and methanol was added for recrystallization to obtain 20.22 g of yellow solid 4'-chloro-2-nitrobiphenyl with a content of 98% and a yield of 84.8%.

[0049] In the present embodiment, the preparation process of oxidizing agent is as follows:

[0050] Weigh 31.6g (0.2mol) of potassium permanganate and dissolve it in 600g of deionized water, and slowly add 480g of 30% hydrogen peroxide solution dropwise under stirring. Use nitric acid and KOH to adjust the reaction system to maintain weak alkalinity (pH=7~9), then add 10 g of nickel nitrate solution containing 1.83 g (10 mmol) dropwise, continue to react for 30 min after the drop...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a preparation method of 4'-chloro-2-nitrobiphenyl. The method comprises the following steps: carrying out dehydrogenation aromatization reaction in an organic solvent at 110-179 DEG C by using 1-chloro-4-(6-nitrocyclohexyl-3-alkenyl)benzene as a raw material and using metal ion doped manganese dioxide as an oxidant to obtain 4'-chloro-2-nitrobiphenyl with the yield of 75.5-84.8% and the content of 98.0-99.6%. The preparation method has the advantages of high yield, low cost, simplicity and convenience in operation, environmental friendliness and the like.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and relates to a preparation method of 4'-chloro-2-nitrobiphenyl, in particular to the preparation of 4'-chloro-2-nitrobiphenyl by using metal ion doped manganese dioxide as an oxidizing agent. Benzene method. Background technique [0002] 4′-Chloro-2-nitrobiphenyl is a key intermediate in the synthesis of boscalid. Boscalid is a new type of nicotinamide fungicide developed by BASF, Germany. Its common name is boscalid, also known as nicobifen, and its test number is BAS510. It is a mitochondrial respiration inhibitor, succinate dehydrogenase inhibitor (SDHI), which acts by inhibiting succinate-CoQ reductase (also known as complex II) on the mitochondrial electron transport chain, and its mechanism of action Similar to other amide and benzamide fungicides, it is mainly used to control powdery mildew, gray mold, various rot, brown rot and root rot, etc. It is active against al...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C201/12C07C201/16C07C205/12
CPCC07C201/12C07C201/16C07C205/12
Inventor 罗先福王燕虞孝云刘国文彭长春杜升华黄幼援
Owner 湖南海利常德农药化工有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com