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

Method for synthesizing biaryl

A biaryl hydrocarbon and halogenated hydrocarbon technology, applied in the field of organic catalysis synthesis, can solve the problems of polluting the environment, high reaction cost, difficult to achieve large-scale production, etc., and achieve the effects of low corrosiveness, less dosage and easy preparation

Active Publication Date: 2017-03-22
YANGZHOU UNIV
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to provide a method for synthesizing biaryls to solve the problems of high reaction cost, environmental pollution and difficulty in large-scale production in the prior art

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
  • Method for synthesizing biaryl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] 1. Prepare the catalyst:

[0013] Weigh 1231.6 mg (10 mol) of p-methoxyaniline and dissolve it in 100 ml of aqueous hydrochloric acid with a concentration of 1 mol / L to obtain solution a.

[0014] Weigh 44.3 mg of palladium dichloride and dissolve in 100 ml of aqueous hydrochloric acid with a concentration of 1 mol / L to obtain solution b.

[0015] Add solution b to solution a, stir for 2 minutes after mixing, and let stand for 24 hours. Adjust the pH value to 7.0 with 1mol / L sodium hydroxide aqueous solution to obtain a flocculent precipitate, which is centrifuged, washed three times with deionized water, and dried at 100°C for 6 hours to obtain a blue-yellow solid, that is, poly-p-methoxyaniline-loaded nanoparticles palladium.

[0016] 2. Synthesis of biaryls:

[0017] In a 50 ml reaction tube, add 6 mg poly-p-methoxyaniline supported nano-palladium catalyst, 2.04 g (10 mmol) iodobenzene, 589 mg (10 mmol) hydrazine hydrate (85%), 1.29 g (10 mmol) di Isopropylethyla...

Embodiment 2

[0019] Other conditions are the same as in Example 1, and the influence of the reaction temperature on the reaction is checked, and the experimental results are as shown in Table 1.

[0020] Table 1 Effect of reaction temperature

[0021] Reaction temperature (°C) 80 130 140 150 Product yield (%) 7.3 52.3 70.3 53.3

[0022] It can be seen from the above table that the effect is the best and the yield is the highest when the reaction temperature is 140°C.

Embodiment 3

[0024] Other conditions are the same as in Example 1, and the influence of the consumption of the reducing agent hydrazine hydrate on the reaction is checked, and the experimental results are shown in Table 2.

[0025] Table 2 The effect of reducing agent hydrazine hydrate dosage

[0026] Hydrazine hydrate / mmol 0 0.5 1.0 2.0 Product yield (%) 41.0 39.8 70.3 14.0

[0027] It can be seen from the above table that the yield is the highest when the molar ratio of reducing agent hydrazine hydrate to iodobenzene is 1:1.

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 provides a method for synthesizing biaryl and belongs to the field of organic catalytic synthesis. Poly p-anisidine loaded nano-palladium serves as a catalyst, diisopropylethylamine serves as an alkali, in a N-methyl pyrrolidinone solvent, and the reduction of halohyrocarbons with hydrazine hydrate is catalyzed to prepare biaryl. According to the method, the reaction condition is mild, products are easy to separate, the reaction is easy to operate, and good safety is achieved. Secondly, the catalyst used in the method is easy to prepare, the use amount is small, and after the reaction is completed, the catalyst can be recycled for many times. In addition, in the method, the green alkali and the green reduction agent are used, solid waste is little, corrosivity is low, and the method is green and environmentally friendly, and protects the environment.

Description

technical field [0001] The invention belongs to the field of organic catalytic synthesis. Background technique [0002] Biaryls are an important class of organic compounds, which widely exist in natural products, medicines, dyes, functional polymers, organic conductors and semiconductors. In 1901, German chemist Ullmann discovered that aryl halides could be used to prepare symmetrical biaryls under the catalysis of active copper powder. However, the reaction conditions were very harsh and required high temperatures (generally greater than 200 o C), and use excessive copper catalysis, although it has been improved by people in various experiments, it also faces many problems, such as large amount of catalyst, difficult to recycle, complex reducing agent, etc., which makes the reaction cost high And pollute the environment, not suitable for large-scale production. Contents of the invention [0003] The purpose of the present invention is to provide a method for synthesizin...

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): C07C1/26C07C15/14
CPCY02P20/584C07C1/26C07C2523/44C07C2531/06
Inventor 俞磊刘永红唐大亮刘名轩
Owner YANGZHOU UNIV
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