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Preparation method of diaryl ether compound

A compound and aryl technology, applied in the field of preparation of diaryl ether compounds, can solve the problems of generating solid waste, toxicity, corrosion, etc., and achieve the effects of zero discharge of three wastes, mild reaction conditions, and production cost saving

Active Publication Date: 2019-05-17
YANCHENG TEACHERS UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This type of reaction conditions still has its application limitations, such as corrosion, toxicity, difficulty in catalyst handling, difficulty in separating from the reaction system, and generation of solid waste, etc.

Method used

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  • Preparation method of diaryl ether compound
  • Preparation method of diaryl ether compound
  • Preparation method of diaryl ether compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] In a 50ml reaction bottle, add 0.1g of copper oxide nanoparticles, 1g of chitosan and 20ml of toluene, sonicate to obtain a uniform suspension, and stir at room temperature to ensure that the chitosan surface adsorbs enough Cu2O nanoparticles, filter, Washed with ethanol and dried under vacuum at 50 °C to obtain CS-supported Cu 2 O(CS@Cu 2 O). Refer to this method to prepare CS@CuSO 4 , CS@CuI and CS@Cu(OAc) 2 to spare.

Embodiment 2

[0052]

[0053] Add bromobenzene, phenol, catalyst, alkali and solution to the reaction in sequence, heat and stir for 18 hours, add water to quench the reaction, filter, use for ethyl acetate extraction, wash with saturated brine, dry, concentrate, and perform silica gel column chromatography in diphenyl ether. To investigate the catalyst effectiveness of different reaction conditions, the specific data are as described in Table 1:

[0054] Table 1

[0055]

[0056]

[0057] a General reaction conditions: 1.5mmol phenol, 1.0mmol bromobenzene, 2.0mmol potassium phosphate, 1mL of anhydrous solvent; b3.0mmol potassium phosphate; c 2mmol phenol.

[0058] Conclusion: Using the coupling reaction of bromobenzene and phenol as a template, the catalytic effects of different catalysts (A, B, C, D) were preliminarily evaluated. When 0.01 equivalent of [Cu] and 2 equivalents of K are present in DMF 3 PO 4 When , the coupling reaction of p-bromobenzene and phenol showed good ...

Embodiment 3

[0060]

[0061] Add 1mmol formula II compound, 2mmol formula III compound, 0.5mmol% catalyst CS@Cu to the reaction successively 2 O. 3mmol potassium phosphate and 0.5ml N,N-dimethylformamide solution, heated to 110°C and stirred for reaction. After the reaction was detected by TLC, add water to quench the reaction, filter, use for ethyl acetate extraction, and wash with saturated saline , dried, concentrated, and silica gel column chromatography to obtain diphenyl ether.

[0062]

[0063]

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Abstract

The invention relates to a preparation method of a diaryl ether compound. Particularly, under catalysis of chitosan supported cuprous oxide, an arylation reaction used for phenols is achieved, the corresponding diaryl ether compound is obtained, the technological condition is simple, the yield is good, operability is high, and wide functional group durability is achieved.

Description

technical field [0001] The invention belongs to the field of chemical industry and medicine, and relates to a preparation method of diaryl ether compounds. Background technique [0002] Aryl ethers are valuable compounds in the fields of organic synthesis, medicine or biology. One of the most common preparation methods is the Ullmann-type coupling reaction. In order to solve the problems of long reaction time, high temperature (>200°C) and the stoichiometric ratio of copper required for the catalyst, organic chemists screened different ligands to achieve aryl bromides and aryl bromides under mild conditions. Iodide coupling with phenol and imidazole. This type of reaction conditions still has its application limitations, such as corrosion, toxicity, difficulty in catalyst handling, difficulty in separating from the reaction system, and generation of solid waste. [0003] Immobilizing catalysts on heterogeneous supports is one of the main strategies to solve the above p...

Claims

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Application Information

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IPC IPC(8): C07C41/16C07C43/275C07C43/263C07C43/29C07C45/64C07C49/84B01J31/28
Inventor 钱存卫冯雪馨杨子健胡朝俊邱悦王庆东杨锦明
Owner YANCHENG TEACHERS UNIV
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