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

O-aminobiphenyl compound synthesis method

A technology for o-aminobiphenyl and compounds, which is applied in the field of synthesizing o-aminobiphenyl compounds, can solve the problems of difficult industrial acquisition of raw materials, high preparation or high price, harsh reaction conditions, etc., and achieves reduced production costs, simple operation, and comprehensive synthetic routes short effect

Active Publication Date: 2017-12-19
SHANGHAI XIAOMING DETECTION TECH SERVICE CO LTD
View PDF16 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0022] It can be seen from the above that there are harsh reaction conditions in the method for preparing o-aminobiphenyl compounds in the prior art, the raw materials are difficult to obtain industrially, the preparation or the price is high, the amount of three wastes is large, the separation and purification are difficult, the operation is complicated, or two or more steps are required Shortcomings such as synthesis of o-aminobiphenyl compounds in the reaction steps

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
  • O-aminobiphenyl compound synthesis method
  • O-aminobiphenyl compound synthesis method
  • O-aminobiphenyl compound synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Example 1 3',4'-Dichloro-2-amino-5-fluorobiphenyl

[0064] (1) Preparation of 2-nitro-5-fluorobenzoate

[0065] Add 111.0g of 2-nitro-5-fluorobenzoic acid (with a mass percentage of 99%, within 100g directly from Huaian Ping An Chemical Co., Ltd., and prepare a large amount according to the method described in US 5591890) in a 2L three-necked bottle, 600mL without Water ethanol, add potassium hydroxide ethanol solution dropwise at room temperature (38.9g of 85% by mass potassium hydroxide dissolved in 600mL absolute ethanol), stir at room temperature for 2 hours, during this process a large amount of light yellow solid precipitates , Filtered and dried to obtain 123.6 g of light yellow powdery solid potassium salt of 2-nitro-5-fluorobenzoic acid with a mass percentage of 99%.

[0066] (2) Preparation of 3',4'-dichloro-2-amino-5-fluorobiphenyl

[0067] Add 13.38 g (0.06 mol) 2-nitro-5-fluorobenzoic acid potassium salt, 0.22 g (0.0012 mol) cuprous iodide, 0.12 g (0.0004 mol) to ...

Embodiment 36

[0079] Into a dry 250 ml three-necked flask equipped with a magnetic stirrer were added 13.38 g of 2-nitro-5-fluorobenzoic acid potassium salt, 0.22 g of cuprous iodide, 0.12 g of palladium acetylacetonate, 0.36 g of 1,10 -Phenanthroline, 8.44 grams of 3,4-dichlorobromobenzene, 3 grams of 3A molecular sieve, and 80 grams of anhydrous polyethylene glycol PEG-400, and then nitrogen vacuum replacement three times, under the protection of nitrogen, stirring and heating to 190 ℃, react for 23 hours. Use gas chromatograph or high pressure liquid chromatograph to detect the end of the reaction, cool the reaction solution to room temperature, filter, add 120 ml of water to the filtrate to evenly dilute, extract 3 times with toluene (60 ml / time), combine the extracts and wash them with water (100 ml / time), the organic phase was concentrated with a rotary evaporator, the oily mixture obtained was recrystallized with petroleum ether, and after filtration, a yellow 3',4'-dichloro-2-amino-5...

Embodiment 37

[0081] Into a dry 250 ml three-necked flask equipped with a magnetic stirrer were added 13.38 g of 2-nitro-5-fluorobenzoic acid potassium salt, 0.22 g of cuprous iodide, 0.12 g of palladium acetylacetonate, 0.36 g of 1,10 -Phenanthroline, 8.44 grams of 3,4-dichlorobromobenzene, 3 grams of 3A molecular sieve, and 80 grams of anhydrous trimethylbenzene, and then nitrogen vacuum replacement three times, under the protection of nitrogen, stirring and heating to 190 ℃, reaction for 23 hours . After the reaction is detected by gas chromatograph or liquid chromatograph, the reaction liquid is cooled to room temperature, filtered, 120 ml of water and 150 ml of trimethylbenzene are added to the filtrate, and the mixture is stirred evenly. The organic phase is separated and washed with water (100 ml / time) The organic phase was concentrated twice with a rotary evaporator. The oily mixture obtained was recrystallized with petroleum ether. After filtration, 10.40 g of yellow 3',4'-dichloro-...

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 relates to an o-aminobiphenyl compound synthesis method, which comprises: carrying out a reaction on an o-nitroaromatic formic acid compound, an alkali and a solvent, removing water, adding substituted halobenzene, a catalyst and a ligand, carrying out a reaction, or carrying out a reaction on a pre-prepared o-nitroaromatic formate, substituted halobenzene, a catalyst, a ligand and a solvent, and carrying out post-treatment to obtain the o-aminobiphenyl compound. According to the present invention, the o-aminobiphenyl compound is synthesized by using the easily available or easily prepared o-nitroaromatic formate and the substituted halobenzene as the raw material through the one-step method without the use of hydrogen and other hazardous reducing agents, such that the coupling and nitro reduction continuous reaction is achieved, and the advantages of new reaction, safety, high efficiency, simple operation and low cost are provided.

Description

Technical field [0001] The invention belongs to the field of pesticide compound synthesis, and particularly relates to a method for synthesizing o-aminobiphenyl compounds. Background technique [0002] O-aminobiphenyl compounds are the key intermediates used in the preparation of the commercially valuable bixflufen and fluconazole. [0003] Bixafen is a pyrazole or amide broad-spectrum fungicide (see CN 1646494A) discovered by Bayer Crop Science AG in Germany in 2003, and its chemical name is N-(3',4'-dichloro- 5-Fluoro[1,1'-biphenyl]-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, which can be used for powdery mildew, rust and downy mildew Prevention and treatment of various diseases. It went public in 2011 and its sales in 2012 reached more than 100 million U.S. dollars. Bayer CropScience Co., Ltd. expects its peak sales to reach more than 400 million U.S. dollars. [0004] Fluconazole is a pyrazole or amide broad-spectrum fungicide (see CN 101115723A) discovered by G...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/00C07C211/52
CPCC07C209/00C07C211/52
Inventor 张照军王淼张浩谢思勉田晓宏
Owner SHANGHAI XIAOMING DETECTION TECH SERVICE CO LTD
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