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Dibenzofuran derivative and preparation method thereof

A technology of furan derivatives and dibenzofuran, which is applied in the field of dibenzofuran derivatives and its preparation, can solve the problems of poor selectivity, high cost, cumbersome routes, etc., and achieve convenient post-processing, low cost and good compatibility Effect

Pending Publication Date: 2018-12-18
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In order to overcome the shortcomings of existing dibenzofuran compounds such as cumbersome routes, high cost, and poor selectivity, the present invention provides a one-pot method for preparing dibenzofuran compounds, which is synthesized by simple o-dibromobenzene derivatives and phenol derivatives Diaryl ether compounds, and then obtain dibenzofuran compounds under metal-catalyzed conditions

Method used

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  • Dibenzofuran derivative and preparation method thereof
  • Dibenzofuran derivative and preparation method thereof
  • Dibenzofuran derivative and preparation method thereof

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preparation example Construction

[0015] The preparation route of dibenzofuran derivatives is as follows, using ortho-dibromobenzene derivatives and phenol derivatives as starting materials, through substitution reaction and ring closure reaction process, finally generating dibenzofuran isoindigo derivatives, See Examples 1-6 for details.

[0016]

Embodiment 1

[0018] The synthetic route of 3-methoxydibenzofuran is as follows:

[0019]

[0020] Add o-dibromobenzene (0.235g, 1mmol), m-methoxyphenol (0.148g, 1.2mmol), potassium carbonate (0.069g, 0.5mmol) and copper oxide (0.079g, 1mmol) into a 25mL single-necked round bottom flask Dissolve in 5mL DMF, react under reflux for 3 hours with stirring, cool to room temperature, filter with suction, and collect the filtrate. Under nitrogen protection, the filtrate, Pd(OAc) 2 (0.011g, 5%mmol), PCy 3 ·HBF 4 (0.0368g, 10%mmol) and potassium carbonate (0.345g, 2.5mmol) were added into a 25mL three-necked flask, and the reaction system was heated to 130°C for 12 hours. After the reaction was completed, cool to room temperature, add appropriate amount of water, extract with ether, dry over anhydrous sodium sulfate, spin off the solvent, and crystallize with ether to obtain 0.18 g of white solid, with a yield of 91%. 1 H NMR (500MHz, CDCl 3 )δ7.89-7.66(m,3H),7.38-6.98(m,4H),3.83(s,3H). 13 ...

Embodiment 2

[0022] The synthetic route of 2-fluoro-7-methoxydibenzofuran is as follows:

[0023]

[0024] Add o-dibromobenzene (0.253g, 1mmol), m-methoxyphenol (0.148g, 1.2mmol), potassium carbonate (0.069g, 0.5mmol) and copper oxide (0.079g, 1mmol) into a 25mL single-necked round bottom flask Dissolve in 5mL DMF, react under reflux for 3 hours with stirring, cool to room temperature, filter with suction, and collect the filtrate. Under nitrogen protection, the filtrate, Pd(OAc) 2 (0.011g, 5%mmol), PCy 3 ·HBF 4 (0.0368g, 10%mmol) and potassium carbonate (0.345g, 2.5mmol) were added into a 25mL three-necked flask, and the reaction system was heated to 130°C for 12 hours. After the reaction was completed, cool to room temperature, add appropriate amount of water, extract with ether, dry over anhydrous sodium sulfate, spin off the solvent, and crystallize with ether to obtain 0.18 g of white solid with a yield of 83%. 1 H NMR (500MHz, CDCl 3 )δ7.78-7.64(m,2H),7.52-7.35(m,2H),7.22-6.9...

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Abstract

The invention belongs to the technical field of organic optoelectronic materials, and particularly relates to a dibenzofuran derivative and a preparation method thereof. A one-pot method is used for dissolving dibromobenzene and substituted phenol into an organic solvent; backflow reaction is performed for 10 hours; then, intramolecular reaction is performed under the effect of catalyst effects, so as to obtain; the substituted dibenzofuran derivative can be obtained atwith the yield of 80 percent. The method provided by the invention has the advantages that the raw material sources are wide;, and economical performance is realized; the operation is simple and convenient; the product can be easily separated and purified. In addition, the substituted dibenzofuran derivative related byin the invention has the advantages that the multi-functional group substituted products can be simply obtained; the net next derivation can be performed for synthesizing a series of materials based ontaking dibenzofuran as mother bodies; the kind type of material has high power supply performance and conjugacy performance, and is hopeful to be used in the field of an organic photoelectric material.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectricity, and specifically relates to a dibenzofuran derivative and a preparation method thereof. Background technique [0002] Benzofuran derivatives widely exist in natural products, drugs, bioactive molecules and organic functional materials, many of which have good physiological activity and are an important class of organic compounds with dibenzofuran ring skeletons. Dibenzofuran and its derivatives are also important intermediates in organic synthesis, which can be used to synthesize complexes, heterocyclic compounds, drug molecules and various material molecules. Therefore, the synthesis of benzofuran derivatives has always been one of the important research fields in organic synthesis. Substituted dibenzofurans are relatively important benzofuran derivatives, and their synthesis methods are mainly divided into two types: traditional synthesis methods and transition metal-catalyzed...

Claims

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Application Information

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IPC IPC(8): C07D307/91
CPCC07D307/91
Inventor 郭旺军刘英哲张杰刘亚东刘建群伍致生宋新潮王户生
Owner XIAN MODERN CHEM RES INST
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