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Method for preparing diaryl ether compound

A technology for diaryl ethers and compounds is applied in the field of novel preparation of diaryl ether compounds, can solve problems such as high cost, and achieve the effects of simple operation and low cost

Inactive Publication Date: 2019-08-23
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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

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  • Method for preparing diaryl ether compound
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  • Method for preparing diaryl ether compound

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 40 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);

[0028] 13 C NMR (101MHz, CDCl 3 )δ161.71, 154.81, 139.29, 134.29, 134.18, 130.29,

[0029] 125.21, 122.46, 120.47, 118.92, 118.19, 117.93, 105.80.

Embodiment 2

[0031] 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 40 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

[0033] 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 40 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%.

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Abstract

The invention relates to a novel preparation method of a diaryl ether compound. The novel preparation method specifically comprises the following steps: sequentially putting a derivative of benzene, dimethyl sulfoxide, cesium carbonate and a phenol derivative into a reactor, and carrying out stirring for 30-60 minutes at room temperature; putting the mixture into an oil bath pot of which the reaction temperature is set as 70-120 DEG C, lighting the mixture with an incandescent light bulb, detecting the reaction process with TLC (thin layer chromatography), after the reaction is completed, carrying out filtering on a reaction liquid, and carrying out extraction and column chromatography, so as to obtain a target compound and complete preparation of the diaryl ether compound. By adopting thetechnical scheme of the invention, under induction of visible light, without addition of any transition metal catalyst, ligand or photoredox agent, an aryl halide and a phenol derivative are subjected to a photocatalytic C-O cross coupling reaction. The preparation method is mild in condition, green, efficient, low in cost and simple and convenient in operation. The prepared compound is a significant synthesis intermediate in fields such as biologics, medicines and organic synthesis, particularly in medicine synthesis.

Description

technical field [0001] The invention relates to a novel preparation method of a diaryl ether compound, which belongs to the technical field of organic synthesis. 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 no...

Claims

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Application Information

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IPC IPC(8): C07C253/30C07C255/54C07C201/12C07C205/38C07C45/64C07C49/84
CPCC07C45/64C07C201/12C07C253/30C07C255/54C07C205/38C07C49/84
Inventor 王龙刘娜阳青青胡为民
Owner CHINA THREE GORGES UNIV
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