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Method for preparing diphenyl ether compound

A kind of compound, technology of diphenyl ether, applied in the field of preparation of diphenyl ether compounds

Active Publication Date: 2013-04-03
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the traditional method of preparing diphenyl ethers, phenol derivatives must be used, and phenols are moderately strong chemical poisons that chemically react with proteins in the cell protoplasm

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment one: a kind of method for preparing 4,4'-diacetyl biphenyl ether, comprises the following processing steps:

[0018] Add p-fluoroacetophenone (6.90mg, 0.05mmol), pinacol diborate (20.32mg, 0.08mmol), copper chloride (0.34mg, 5%*0.05mmol), 1,2 - Bis(diphenylphosphine)ethane (3.98mg, 20%*0.05mmol), cesium carbonate (6.52mg, 40%*0.05mmol). Add the reaction solvent DMF, the reaction temperature is 150°C, the reaction time is 20h, the yellow solution produced is dissolved in water, and then extracted with ethyl acetate, the solution of the ethyl acetate layer is retained, suspended to dryness, and then separated with a 200-300 mesh silica gel column (washing Deagent is ethyl acetate / normal hexane of 1: 2), after removing solvent, obtain 4,4'-diacetyl biphenyl ether, structural formula is:

[0019] Yield 68%, melting point: 98-100°C.

Embodiment 2

[0020] Embodiment two: a kind of method for preparing 4,4'-dicyanodiphenyl ether comprises the following processing steps:

[0021] Add p-fluorobenzonitrile (6.06mg, 0.05mmol), biboronic acid pinacol ester (12.7mg, 0.05mmol), aluminum chloride (0.68mg, 10%*0.05mmol), 1,2- Bis(diphenylphosphine)ethane (9.95mg, 50%*0.05mmol), cesium carbonate (6.52mg, 40%*0.05mmol). Add the reaction solvent DMF, the reaction temperature is 80°C, and the reaction time is 24 hours. Dissolve the light yellow solution with water, then extract it with ethyl acetate, keep the solution of the ethyl acetate layer, hang it to dryness, and then separate it with a 200-300 mesh silica gel column ( Eluent is 2: 3 dichloromethane / n-hexane), after removing solvent, obtain 4,4'-dicyanodiphenyl ether, structural formula is:

[0022] Yield: 92%. Melting point: 182°C.

Embodiment 3

[0023] Embodiment three: a kind of method for preparing 4-nitro-4'-aminodiphenyl ether comprises the following processing steps:

[0024] Add p-fluoronitrobenzene (7.06mg, 0.05mmol), pinacol diborate (22.86mg, 0.09mmol), copper chloride (0.68mg, 10%*0.05mmol), 1,2 - Bis(diphenylphosphine)ethane (3.98mg, 20%*0.05mmol), cesium carbonate (6.52mg, 40%*0.05mmol). Add the reaction solvent DMF, the reaction temperature is 45°C, the reaction time is 15h, the dark brown solution produced is dissolved in water, and then extracted with ethyl acetate, the solution of the ethyl acetate layer is retained, suspended to dryness, and then separated with a 200-300 mesh silica gel column ( Eluent is 1: 1 dichloromethane / n-hexane), after removing solvent, obtain 4-nitro-4'-aminodiphenyl ether, structural formula is:

[0025] The yield was 84%. Melting point: 132-133°C.

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PUM

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Abstract

The invention relates to a method for preparing a diphenyl ether compound. The method is characterized by comprising the following technical steps of: (1) adding a halogenated benzene derivative and a bis(pinacolato)diboron into a reaction vessel, adding copper chloride or aluminum chloride and 1,2-bi(diphenylphosphine) ethane as a catalyst, then adding alkaline and an organic solvent, and reacting at 25-160 DEG C for 6-24 hours; and (2) after extracting a reaction solution obtained from the step (1) by using ethyl acetate, purifying by a 200-300 meshes silica gel column, pre-eluting the silica gel column by using 20-50 mL of normal hexane, eluting by adopting an eluent at a flow speed of 1-2 mL / min for 3-6 hours, and removing the solvent to obtain the diphenyl ether compound. The method for preparing the diphenyl ether compound, disclosed by the invention, no only overcomes the disadvantage of the use of phenolic substances in a reaction process, but also has the advantages of mild reaction condition and high yield.

Description

technical field [0001] The invention relates to a method for preparing biphenyl ether compounds, belonging to the technical field of chemical materials and medicines. Background technique [0002] Since Rohn&Hass discovered the first diphenyl ether herbicide in 1960, the synthesis and biological activity of this kind of compound have received great attention. Studies have shown that it has anti-tumor activity, anti-plant virus, anti-microalgae, herbicide, bactericidal, anti-inflammatory, fish poisoning, and inhibits important biological activities such as angiotensin converting enzyme, aminopeptidase, HIV protease, and pectinase . In 1964, Geigy reported the new synthesis of broad-spectrum antibacterial agent trichloro. It is a phenolic antibacterial agent with low toxicity, high efficiency, broad spectrum and excellent performance. It has a wide range of killing and inhibiting effects on Gram-positive bacteria, Gram-negative bacteria, yeast and viruses, antibiotic bacter...

Claims

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Application Information

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IPC IPC(8): C07B41/04C07C45/64C07C49/84C07C201/12C07C205/23C07C205/26C07C213/00C07C215/76C07C253/30C07C255/54C07C41/01C07C43/29
Inventor 丁玉强陈建平王大伟
Owner JIANGNAN UNIV
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