Unlock instant, AI-driven research and patent intelligence for your innovation.
Novel preparation method of diaryl ether compound and application thereof
What is Al technical title?
Al technical title is built by PatSnap Al team. It summarizes the technical point description of the patent document.
A technology of diaryl ethers and compounds, which is applied in the new preparation and application fields of diaryl ether compounds, can solve problems such as high cost, and achieve the effect of simple operation and low cost
Inactive Publication Date: 2019-06-14
CHINA THREE GORGES UNIV
View PDF3 Cites 3 Cited by
Summary
Abstract
Description
Claims
Application Information
AI Technical Summary
This helps you quickly interpret patents by identifying the three key elements:
Problems solved by technology
Method used
Benefits of technology
Problems solved by technology
[0004] The main purpose of the present invention is to overcome the shortcomings of traditional synthesis of diaryl ether compounds such as high cost, to provide a diaryl ether compound that does not require any transition metal catalysts and ligands or photoredox agents, and only needs to be induced by visible light The green synthesis method of
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
Click on the blue label to locate the original text in one second.
Reading with bidirectional positioning of images and text.
Smart Image
Examples
Experimental program
Comparison scheme
Effect test
Embodiment 1
[0024] A method for preparing 4-cyano diaryl ether (4-phenoxybenzonitrile) 3a, comprising the following experimental steps:
[0025] In the reactor, add compound 4-cyanoiodobenzene 1a (0.23g, 1.0mmol, 1.0eqv.), DMSO (3ml), Cs 2 CO 3 (0.65g, 2.0mmol, 2.0eqv.), phenol 2a (0.113g, 1.2mmol, 1.2eqv.), stirred at room temperature for 10 minutes. Then put it in an oil bath at 80°C and react under light for 10 h. After the reaction was detected by TLC, the reaction liquid was filtered, extracted and column chromatographed to obtain the target product 3a with a yield of 79%.
[0026]
[0027] 1 H NMR (CDCl 3 ,400MHz,)δ(ppm)7.60(d,J=8.0Hz,2H,Ar-H),7.44-7.40(m,2H,Ar-H),7.26-7.23(m,1H,Ar-H), 7.08(m,2H,Ar-H),7.00(m,2H,Ar-H);
[0030] In the reactor, add compound 4-cyanoiodobenzene 1a (2.3g, 10mmol, 1.0eqv.), DMSO (30ml), Cs 2 CO 3 (6.5g, 20mmol, 2.0eqv.), phenol 2a (1.13g, 12mmol, 1.2eqv.), stirred at room temperature for 10 minutes. Then put it in an oil bath at 80°C and react under light for 10 h. After the reaction was detected by TLC, the reaction solution was filtered, extracted and column chromatographed to obtain the target product 3a with a yield of 76%.
Embodiment 3
[0032] In the reactor, add compound 4-cyanoiodobenzene 1a (0.023g, 0.10mmol, 1.0eqv.), DMSO (0.3ml), Cs 2 CO 3 (0.065g, 0.20mmol, 2.0eqv.), phenol 2a (0.0113g, 0.12mmol, 1.2eqv.), stirred at room temperature for 10 minutes. Then put it in an oil bath at 80°C and react under light for 10 hours. After the reaction was detected by TLC, the reaction solution was filtered, extracted and column chromatographed to obtain the target product 3a with a yield of 83%.
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
Login to View More
Abstract
The invention provides a novel preparation method of a diaryl ether compound. The method concretely comprises the steps of sequentially adding a compound 1, dimethyl sulfoxide, cesium carbonate and acompound 2 into a reactor; performing stirring for 10 to 60 minutes at room temperature; then, putting the materials into an oil bath pot with the reaction temperature of 70 to 120 DEG C; performing illumination by an incandescent light bulb; performing TLC detection on the reaction process; after the reaction is completed, performing filtering, extraction and column chromatography on reaction liquid to obtain a target compound; completing the preparation of the diaryl ether compound. By using the technical scheme, under the visible light induction, no transition metal catalyst and no ligand or photooxidant reducing agent are added; arylhalide and phenol derivatives take photocatalysis C-O crossed coupling reaction. The preparation method has the advantages that the conditions are mild and green; the efficiency is high; the cost is low; the operation is simple and convenient. The prepared compound is an important synthetic intermediate in the fields of biology, medicine and organic synthesis, particularly in an aspect of medicine synthesis.
Description
technical field [0001] The invention relates to a novel preparation method of a diaryl ether compound and an application example thereof. Background technique [0002] Diaryl ether compounds have played an important role in the field of organic synthesis for many years, and are also important synthetic intermediates in medicine and pesticides. Some organic compounds composed of diaryl ether units, such as the antibiotic vancomycin and HIV antibiotics, have been shown to have significant biological activity. However, the traditional synthesis methods of diaryl ether intermediates have disadvantages such as high cost, low efficiency, complicated process operation and the like. Therefore, it is imperative to seek a new, simple and efficient synthetic method. Contents of the invention [0003] The patent of the present invention proposes a new method for synthesizing diaryl ether compounds with mild conditions and high efficiency. This method does not require any transition...
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
Application Date:The date an application was filed.
Publication Date:The date a patent or application was officially published.
First Publication Date:The earliest publication date of a patent with the same application number.
Issue Date:Publication date of the patent grant document.
PCT Entry Date:The Entry date of PCT National Phase.
Estimated Expiry Date:The statutory expiry date of a patent right according to the Patent Law, and it is the longest term of protection that the patent right can achieve without the termination of the patent right due to other reasons(Term extension factor has been taken into account ).
Invalid Date:Actual expiry date is based on effective date or publication date of legal transaction data of invalid patent.
Login to View More 
Login to View More 
