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Method for synthesizing asymmetric diaryl ether derivative

A technology of diaryl ether and synthesis method, applied in ether preparation, organic chemistry and other directions, to achieve the effects of mild reaction conditions, good product quality, advanced and reasonable process route

Inactive Publication Date: 2012-07-04
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the disadvantage is that the reaction can only be carried out in the presence of some ligands with complex structures and expensive palladium catalysts.

Method used

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  • Method for synthesizing asymmetric diaryl ether derivative
  • Method for synthesizing asymmetric diaryl ether derivative
  • Method for synthesizing asymmetric diaryl ether derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] According to the molar ratio of aryl boric acid, nitrobenzene compound, copper catalyst, additive, and basic compound, feeding is 1.0:2.0:0.05:1.0:3.0; aryl boric acid is phenylboric acid, and the feeding quality is 12.2g (0.1mol); The base benzene compound is p-nitrobenzaldehyde, and the feeding quality is 30.2g (0.2mol); the copper catalyst is copper oxide, and the feeding quality is 0.40g (0.005mol); the additive is potassium hydrogen persulfate compound salt, and the feeding quality is 61.5g (0.1 mol); the basic compound is cesium carbonate, and the feeding quality is 97.7g (0.3mol); the organic solvent is N,N-dimethylformamide 183g, and its total consumption is 15 times of the quality of phenylboronic acid.

[0028] Put phenylboronic acid, p-nitrobenzaldehyde, copper oxide, potassium persulfate compound salt, and cesium carbonate into the reaction kettle, add N,N-dimethylformamide to dissolve, the reaction temperature is 100°C, and react after 48 hours Finish.

[...

Embodiment 2

[0032] According to phenylboronic acid, p-nitrobenzaldehyde, copper catalyst, potassium persulfate compound salt, cesium carbonate molar ratio is 1.0: 2.0: 0.05: 1.0: 3.0 feeding, phenylboric acid 12.2g (0.1mol); p-nitrobenzene 30.2g (0.2mol) of formaldehyde; 1.0g (0.005mol) of copper acetate; 61.5g (0.1mol) of potassium hydrogen persulfate compound salt; 97.7g (0.3mol) of cesium carbonate; the organic solvent is N,N-dimethylformaldehyde Amide 183g, its total consumption is 15 times of the quality of phenylboronic acid.

[0033] All the other are the same as in Example 1, 16.6g of the resulting product 4-phenoxybenzaldehyde, with a yield of 84% and a purity of 98.3%.

Embodiment 3

[0035] According to phenylboronic acid, p-nitrobenzaldehyde, copper catalyst, potassium persulfate compound salt, cesium carbonate molar ratio is 1.0: 2.0: 0.05: 1.0: 3.0 feeding, phenylboric acid 12.2g (0.1mol); p-nitrobenzene 30.2g (0.2mol) of formaldehyde; 1.8g (0.005mol) of copper trifluoromethanesulfonate; 61.5g (0.1mol) of potassium persulfate compound salt; 97.7g (0.3mol) of cesium carbonate; the organic solvent is N, N- Dimethylformamide 183g, its total consumption is 15 times of the quality of phenylboronic acid.

[0036] The rest are the same as in Example 1, 9.7 g of the resulting product 4-phenoxybenzaldehyde, a yield of 49%, and a purity of 98.7%.

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Abstract

The invention discloses a method for synthesizing asymmetric diaryl ether derivative with a structure shown in a structural formula (I), comprising the following steps: making arylboronic acid and nitrobenzene compound which are raw materials to fully react in an inert organic solvent in the presence of a copper catalyst, an additive and an alkaline compound at 30-150 DEG C, wherein the arylboronic acid has the structural formula (II), and the nitrobenzene compound has the structural formula (III); and postprocessing, separating and purifying a reaction solution after the reaction finishes to obtain the asymmetric diaryl ether derivative. The method for synthesizing the asymmetric diaryl ether derivative has the advantages of mild reaction condition, high reaction yield, good selectivity and low-cost generation cost.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of an unsymmetrical diaryl ether derivative. (2) Background technology [0002] Diaryl ether fragments commonly exist in natural products, pharmaceuticals and chemical products. Because diaryl ether compounds are compounds with good biological and pharmacological activities, they are widely used in the synthesis of pesticides and medicines. It plays an active role in receptor antagonist and anti-tumor, and has high practical value. [0003] In the prior art, the most common method for synthesizing diaryl ether compounds is through the Ullmann coupling method of aryl halides and phenols. However, this method needs to be under harsh conditions, and usually requires metered copper powder or copper catalyst; and for substrates containing sensitive groups, there are many side reactions and low atom economy. In recent years, transition metal-catalyzed cross-coupling reactions of aryl halides and phen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/263C07C41/01C07C43/275C07C47/575C07C205/38C07C255/50
Inventor 吴华悦陈久喜刘妙昌高文霞丁金昌
Owner WENZHOU UNIVERSITY
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