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Method for synthesizing biphenyl compound by taking phenol as raw material

A compound and phenol technology, applied in the field of synthesizing biphenyl compounds, can solve the problems of toxic reagents and expensive raw materials, and achieve the effects of simplified operation, low price and reduced production cost

Inactive Publication Date: 2020-07-03
ZUNYI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Aiming at the problems of expensive raw materials and toxic reagents in the preparation of biphenyl compounds in the prior art, the present invention provides a method for efficiently synthesizing biphenyl compounds without adding ligands and using substituted phenol as a reaction raw material

Method used

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  • Method for synthesizing biphenyl compound by taking phenol as raw material
  • Method for synthesizing biphenyl compound by taking phenol as raw material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1: the preparation of 4-nitrobiphenyl

[0019] In the air, sequentially add 1mmol of 4-nitrophenol, 3mmol of triethylamine, and 4mL of 50% ethanol aqueous solution into a 10mL flask, slowly introduce sulfonyl fluoride gas, and magnetically stir the reaction at room temperature. After 4 hours of reaction, Add 1mmol of phenylboronic acid, 3mmol of triethylamine, 0.1mmol of palladium acetate to the reaction, and continue to react at room temperature for 6 hours. After the reaction is completed, add 20mL of saturated saline to quench the reaction, and the reaction mixture is extracted with 40mL of ethyl acetate. The organic phase and the filtrate were concentrated, and the concentrated filtrate was separated by column chromatography to obtain the final product. The structure of the product was identified by proton nuclear magnetic resonance and mass spectrometry, and the separation yield reached 94%.

[0020] 1 H NMR (400MHz, CDCl 3 )δ8.30(d, J=8.9Hz, 2H), 7.74...

Embodiment 2

[0021] Embodiment 2: the preparation of 4-aminobiphenyl

[0022] In the air, sequentially add 1mmol of 4-aminophenol, 3mmol of triethylamine, and 4mL of 50% ethanol aqueous solution into a 10mL flask, slowly introduce sulfonyl fluoride gas, and magnetically stir the reaction at room temperature. After 4 hours of reaction, the reaction Add 1mmol of phenylboronic acid, 3mmol of triethylamine, 0.2mmol of palladium acetate, and continue to react at room temperature for 6 hours. After the reaction is completed, add 20mL of saturated saline to quench the reaction. The reaction mixture is extracted with 40mL of ethyl acetate. phase, the filtrate was concentrated, and separated by column chromatography to obtain the final product. The structure of the product was identified by proton nuclear magnetic resonance and mass spectrometry, and the separation yield reached 91%. 1 HNMR (400MHz, CDCl 3 )δ7.53(d, J=6.9Hz, 2H), 7.41(t, J=9.5Hz, 4H), 7.34–7.06(m, 1H), 6.75(d, J=7.2Hz, 2H), 3.71( ...

Embodiment 3

[0023] Embodiment 3: the preparation of 3-aminobiphenyl

[0024] In the air, sequentially add 1mmol of 3-aminophenol, 3mmol of triethylamine, and 4mL of 50% ethanol aqueous solution into a 10mL flask, slowly introduce sulfonyl fluoride gas, and magnetically stir the reaction at room temperature. After 4 hours of reaction, the reaction Add 1mmol of phenylboronic acid, 3mmol of triethylamine, 0.2mmol of palladium acetate, and continue to react at room temperature for 6 hours. After the reaction is completed, add 20mL of saturated saline to quench the reaction. The reaction mixture is extracted with 40mL of ethyl acetate. phase, the filtrate was concentrated, and separated by column chromatography to obtain the final product. The structure of the product was identified by proton nuclear magnetic resonance and mass spectrometry, and the separation yield reached 91%.

[0025] 1 H NMR (400MHz, CDCl 3 )δ7.55(d, J=7.1Hz, 2H), 7.40(t, J=7.5Hz, 2H), 7.31(t, J=7.3Hz, 1H), 7.20(t, J=7.8...

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Abstract

The invention discloses a method for synthesizing a biphenyl compound by using phenol as a raw material in the technical field of organic chemical synthesis, which comprises the following steps: carrying out a mixed reaction process on phenol or substituted phenol, alkali and 50-90% ethanol aqueous solution, slowly introducing sulfonyl fluoride gas, and carrying out magnetic stirring reaction at normal temperature for 4-12 hours, adding arylboronic acid, alkali and a palladium catalyst into a round-bottom flask, continuing to react for 6-12 hours at normal temperature, after the reaction is finished, adding a saturated edible salt solution into the round-bottom flask, carrying out a water quenching reaction process to obtain a reaction mixture, extracting a reaction product from the reaction mixture by using ethyl acetate, combining organic phases, concentrating filtrate, and separating the concentrated filtrate by using column chromatography to obtain analytically pure biphenyl or terphenyl compounds. By using the method, on one hand, the production cost of the biphenyl compound is reduced, and on the other hand, the method also has a wide application prospect in the aspects of synthesis of natural products, medicines, pesticides, herbicides, polymer conduction materials, liquid crystal materials and the like.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a method for synthesizing biphenyl compounds by using phenol as a raw material. Background technique [0002] Biphenyl compounds widely exist in medicine, pesticides, natural products and a variety of organic functional materials, and have important application value. Therefore, the development of efficient and green methods for synthesizing biphenyl compounds has always been a research hotspot in academia and industry. . At present, palladium-catalyzed Suzuki cross-coupling reaction (Suzuki reaction) of haloarenes and arylboronic acids is one of the most effective methods for the synthesis of biphenyls, which has the advantages of mild reaction conditions and strong functional group tolerance. However, there are still many deficiencies in the Suzuki cross-coupling reaction: 1) The most commonly used electrophile in the reaction is halogenated aren...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C205/06C07C201/12C07C211/45C07C209/68C07C255/50C07C253/30C07C49/784C07C45/71C07C47/546C07C47/55C07C47/575C07C43/205C07C41/30C07C255/54C07C49/86C07C255/56
CPCC07C201/12C07C209/68C07C253/30C07C45/71C07C41/30C07C205/06C07C211/45C07C255/50C07C49/784C07C47/546C07C47/55C07C47/575C07C43/205C07C255/54C07C49/86C07C255/56
Inventor 李新民张婷婷胡瑞袁泽利
Owner ZUNYI MEDICAL UNIVERSITY
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