Novel preparation method of diaryl ether compound and application thereof
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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
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[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 eth
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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%.
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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; aryl halide 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...
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