Check patentability & draft patents in minutes with Patsnap Eureka AI!

Method for preparing carboxylate aryl type compound

A technology of aryl carboxylate and compounds, which is applied in the field of preparation of aryl carboxylate compounds, can solve the problems of limited application range of substrates and low reaction yield, and achieve wide application range of substrates and high yield Effect

Active Publication Date: 2020-01-14
PEKING UNIV SHENZHEN GRADUATE SCHOOL
View PDF2 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The main purpose of the present invention is to provide a kind of preparation method of aryl carboxylate compound, to solve the technical problems such as limited scope of application of substrates and low reaction yield 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 preparing carboxylate aryl type compound
  • Method for preparing carboxylate aryl type compound
  • Method for preparing carboxylate aryl type compound

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0041] A kind of preparation method of carboxylic acid aryl ester compound, comprises the following steps:

[0042] S01, providing compound A shown in formula a, compound B shown in formula b, organic palladium complexes, and silver salts; the organic palladium complexes are formed by complexing palladium compounds and nitrogen-containing ligands. Nitrogen ligands include: o-phenanthroline compounds and / or bipyridine compounds;

[0043]

[0044] S02, the compound A, the compound B, the organopalladium complex and the silver salt are mixed in a reaction solvent, and reacted under an inert gas atmosphere to obtain the aromatic carboxylic acid as shown in formula I base ester compounds;

[0045]

[0046] where the R 1 Alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, alkoxy, alkenyl, heteroalkenyl, cycloalkenyl, heterocycloalkenyl, aryl, Heteroaryl, aryloxy, heteroaryloxy, arylalkyl, heteroarylalkyl or alkyloxycarbonyl;

[0047] The R 2 , R 3 , R 4 , R 5 , R 6 each...

Embodiment approach

[0082] As an embodiment, the aryl carboxylate compound includes any one of the following compounds:

[0083]

[0084] To sum up, the preparation method of the aryl carboxylate compound provided by the embodiment of the present invention, by cooperating with the organic palladium complex formed by palladium compound and o-phenanthroline compound and / or bipyridine compound and silver salt , and compound A, compound B, organic palladium complexes and silver salts were optimized in terms of raw materials, proportions and reaction conditions, and achieved a high-yield synthesis of aryl carboxylate compounds, with a yield as high as 95%.

[0085] In order to make the above-mentioned implementation details and operation of the present invention clearly understood by those skilled in the art, and the performance of the progress of the preparation method of a kind of aryl carboxylate compound in the embodiment of the present invention is significantly reflected, the following example...

Embodiment 1

[0087] The present embodiment provides a kind of preparation method of phenylbenzoate, and the structural formula of the synthetic phenylbenzoate is as follows:

[0088]

[0089] Its preparation steps are as follows:

[0090] Add palladium trifluoroacetate (0.02mmol, 0.1equiv.), 4,7-dimethoxy-1,10-phenanthroline compound (0.04mmol, 0.2equiv.), trifluoroacetic acid into a dry sealed 15mL tube Silver (0.4mmol, 2.0equiv.), benzoic acid (0.2mmol, 1.0equiv.), iodobenzene (0.4mmol, 2.0equiv.) and 0.4mL trifluorotoluene, replaced by argon three times, stirred at 140°C for 14 hours . After the reaction was completed, the reaction solution was directly spin-dried and separated by column chromatography to obtain the target product precursor, a colorless oily liquid, with a yield of 95%.

[0091] Correlation characterization analysis, the result is: Viscous oil, yield: 95%; 1 H NMR (400MHz, CDCl 3 )δ8.23(d, J=7.5Hz, 2H), 7.65(t, J=7.4Hz, 1H), 7.53(t, J=7.7Hz, 2H), 7.45(t, J=7.9Hz,...

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 belongs to the field of drug synthesis and in particular relates to a method for preparing a carboxylate aryltype compound. The preparation method provided by the invention comprises thefollowing steps: providing a compound A of a formula a shown in the description, a compound B of a formula b shown in the description, an organic palladium complex, and a silver salt, wherein the organic palladium complex is composed of a palladium compound and a nitrogen-containing ligand; the nitrogen-containing ligand comprises an o-phenoline compound and / or a bipyridine compound; and mixing the compound A, the compound B, the organic palladium complex and the silver salt in a reaction solvent, and performing a reaction in an inert gas atmosphere, so as to obtain the carboxylate aryl typecompound of a formula I shown in the description. As the organic palladium complex and the silver salt are simultaneously used, direct selectivity C-O coupling of carboxylic acid and halogenated aromatic hydrocarbon is realized, and the method is applicable to a variety of carboxylic acid substrates and halogenated aromatic substrates, and is wide in compatibility and high in yield.

Description

technical field [0001] The invention belongs to the field of drug synthesis, in particular to a preparation method of aryl carboxylate compounds. Background technique [0002] With the development of chemistry, people have higher and higher requirements for green chemistry, and coupling reactions catalyzed by transition metals play an increasingly important role in chemical synthesis. At the same time, in organic chemical reactions, carbon-heterobonds are ubiquitous, and the rapid and efficient direct coupling of C-O bonds on aromatic rings has always been a research hotspot. Up to now, the direct C-O coupling reaction on aromatic rings has been reported less. [0003] Professor Itomi's research group reported that electron-rich dibenzyl azacarbene was used as the ligand of palladium catalyst to realize the esterification coupling reaction between electron-rich iodobenzene and bulky aliphatic carboxylic acid. The reaction process is as follows. However, the applicable subs...

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): C07B41/12C07C67/11C07C69/78C07C69/75C07C69/608C07C201/12C07C205/57B01J31/22
CPCC07B41/12C07C67/11C07C201/12B01J31/04B01J31/183C07C2601/14C07C2603/74B01J2531/824B01J2231/4288B01J35/19C07C69/78C07C69/75C07C69/608C07C205/57
Inventor 黄湧陈杰安黎黎
Owner PEKING UNIV SHENZHEN GRADUATE SCHOOL
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com