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Method for preparing aryl trifluoroethoxyl ether

A technology for aryl trifluoroethoxy ethers and compounds, which is applied in the field of synthesis of trifluoroethoxy ether compounds, can solve the problems of unsuitability for industrial applications, narrow substrate universality, and high cost, and achieve a synthetic method Simple and efficient, wide substrate applicability, and mild conditions

Inactive Publication Date: 2016-02-24
DONGHUA UNIV +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The technical problem to be solved by the present invention is to provide a method for preparing aryl trifluoroethoxy ether compounds, which solves the problems of high cost, harsh conditions, narrow substrate universality and unsuitability for industrialization in the prior art. Defects such as application

Method used

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  • Method for preparing aryl trifluoroethoxyl ether
  • Method for preparing aryl trifluoroethoxyl ether
  • Method for preparing aryl trifluoroethoxyl ether

Examples

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Effect test

Embodiment 1

[0038] Oxidative Coupling Reaction of 4-Biphenylboronic Acid and Trifluoroethanol Catalyzed by Monovalent Copper Salt Using Air as Oxidant.

[0039]

[0040] Using dichloromethane (5ml) as a solvent, add 4-biphenylboronic acid (0.5mmol), trifluoroethanol (1.0mmol) and triethylamine (1.0mmol) under the catalysis of monovalent copper salt CuTc (0.05mmol), air Stir at room temperature under atmosphere for 18 hours. pass 19 FNMR followed the reaction until the reaction was complete. After filtering, removing the solvent, and separating by column chromatography, the corresponding aryl trifluoroethoxy ether compound was obtained. The yield was 45%. The relevant data are as follows: 1 HNMR (400MHz, CDCl 3 )δppm7.56(d, J=7.2Hz, 4H), 7.43(t, J=7.6Hz, 2H), 7.34(t, J=7.2Hz, 1H), 7.07(d, J=8.4Hz, 2H) ,4.40(q,J=8.2Hz,2H). 13 CNMR (100MHz, CDCl 3 )δppm157.0, 140.4, 135.8, 128.9, 128.4, 127.1, 126.9, 123.5 (q, J=278.0Hz), 115.3, 66.0 (q, J=35.4Hz). 19 FNMR (376MHz, CDCl 3 )δppm-...

Embodiment 2

[0042] Oxidative Coupling Reaction of 4-Biphenylboronic Acid and Trifluoroethanol Catalyzed by Divalent Copper Salt Using Air as Oxidant.

[0043]

[0044] With dichloromethane (5ml) as solvent, add 4-biphenylboronic acid (0.5mmol), trifluoroethanol (1.0mmol) and pyridine (1.0mmol) in divalent copper salt Cu(OAc) 2 (0.05 mmol) catalyzed, stirred at room temperature under air atmosphere for 18 hours. pass 19 FNMR followed the reaction until the reaction was complete. After filtering, removing the solvent, and separating by column chromatography, the corresponding aryl trifluoroethoxy ether compound was obtained with a yield of 55%.

Embodiment 3

[0046] Oxidative Coupling Reaction of 4-Biphenylboronic Acid and Trifluoroethanol Catalyzed by Divalent Copper Salt Using Silver Carbonate as Oxidant.

[0047]

[0048] With dichloromethane (5ml) as solvent, add 4-biphenylboronic acid (0.5mmol), trifluoroethanol (1.0mmol), silver carbonate (1.0mmol) and pyridine (1.0mmol) in divalent copper salt Cu(OAc) 2 (0.05 mmol) catalyzed, stirred at room temperature under nitrogen atmosphere for 18 hours. pass 19 FNMR followed the reaction until the reaction was complete. After filtering and removing the solvent, the corresponding aryl trifluoroethoxy ether compound was obtained by column chromatography separation with a yield of 87%.

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Abstract

The invention relates to a method for preparing aryl trifluoroethoxyl ether. The method includes the steps that aryl boron compounds and trifluoroethanol are added to organic solvent, a copper salt catalyst, a ligand and an oxidizing agent are added, a reaction is conducted in a stirring mode for 1-40 hours at the temperature of 0-60 DEG C, filtering is conducted, column chromatography isolation is conducted, and the aryl trifluoroethoxyl ether is obtained. The method is simple in operation, raw materials are easy to obtain, the reaction condition is mild, the substrate universality is wide, the environmental friendliness is achieved, and the method is applicable to industrial application.

Description

technical field [0001] The invention belongs to the field of synthesis methods of trifluoroethoxy ether compounds, in particular to a method for preparing aryl trifluoroethoxy ether compounds. Background technique [0002] The wide application of fluorine-containing organic compounds in the fields of medicine, pesticides and materials has greatly promoted the introduction of fluorine atoms and various fluorine-containing functional groups into organic molecules. Among these functional groups, trifluoroethoxy group is very common in drug molecules because of its high metabolic stability and good lipophilicity. The marketed drugs include silodosin for the treatment of benign prostatic hyperplasia, flecainide for the treatment of arrhythmia, and lansoprazole for the treatment of duodenal ulcer. The traditional preparation of compounds with such functional groups mainly includes the following two methods: (1) trifluoroethylation of phenolic compounds; (2) nucleophilic substitut...

Claims

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Application Information

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IPC IPC(8): C07C41/01C07C43/225C07C43/29C07C319/20C07C323/20C07C231/12C07C233/25C07C67/31C07C69/92C07C45/64C07C49/84C07C47/575C07C201/12C07C205/37C07C253/30C07C255/54C07C269/06C07C271/16C07D319/08C07D215/20C07D209/86C07D333/76
CPCC07C41/01C07C45/64C07C67/31C07C201/12C07C231/12C07C253/30C07C269/06C07C319/20C07C43/225C07C43/29C07C323/20C07C233/25C07C69/92C07C49/84C07C47/575C07C205/37C07C255/54C07C271/16
Inventor 卿凤翎张柯黄焰根
Owner DONGHUA UNIV
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