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Preparation method of 1'-chloro-8-bromodibenzofuran

A technology of diphenyl and furan, applied in the field of preparation of 1'-chloro-8-bromodibenzofuran, can solve problems such as high price, environmental pollution, and difficulty in obtaining raw materials, and achieve the effect of avoiding acid waste water and solid waste

Inactive Publication Date: 2019-03-19
安徽秀朗新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] This method has the disadvantages that the raw materials are not easy to obtain, the price is expensive, and the use of boron tribromide in the process causes serious environmental pollution, which limits its market application.

Method used

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  • Preparation method of 1'-chloro-8-bromodibenzofuran
  • Preparation method of 1'-chloro-8-bromodibenzofuran

Examples

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Embodiment 1

[0034] The present invention prepares the reaction of 1'-chloro-8-bromodibenzofuran as follows:

[0035]

[0036] The specific process is as follows:

[0037] (1) In a clean and dry 500ml four-necked bottle, introduce nitrogen protection, put 26.1g (0.2mol) m-fluorochlorobenzene and 200ml tetrahydrofuran, start stirring, cool down to -78°C with liquid nitrogen + ethanol, and slowly drop 96ml 2.5mol / L n-butyllithium-n-hexane solution, after the dropwise addition, continue to stir at -78°C for 1h, then slowly add 56.4g (0.3mol) triisopropyl borate dropwise, after the dropwise addition, stir at -78°C After 1h, the temperature was raised to 0°C, and stirring was continued for 2h; 100ml of 2mol / L dilute hydrochloric acid aqueous solution was added dropwise. After the addition was complete, it was stirred at room temperature for 30min, and the layers were separated. The lower aqueous layer was extracted once with 100ml of ethyl acetate. The tetrahydrofuran organic layer was comb...

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Abstract

The invention discloses an efficient and environment-friendly preparation method of 1'-chloro-8-bromodibenzofuran. The preparation method comprises the following steps: (1) pulling out hydrogen from chloro-3-fluorobenzene first with n-butyllithium, then carrying out a substitution reaction with triisopropyl borate and carrying out acid hydrolysis to obtain 2- fluoro-6-chlorophenylboronic acid; (2)carrying out a reaction between 2- fluoro-6-chlorophenylboronic acid and 2-bromophenol under the action of tetra(triphenylphosphine) palladium and potassium carbonate to obtain 2-fluoro-6-chloro-2'-hydroxy-1,1'-biphenyl; (3) carrying out a reaction between 2-fluoro-6-chloro-2'-hydroxy-1,1'-biphenyl and N-bromosuccinimide to obtain 2-fluoro-6-chloro-2'-hydroxy-5'-bromo-1,1'-biphenyl; and (4) carrying out a ring-closure reaction on 2-fluoro-6-chloro-2'-hydroxy-5'-bromo-1,1'-biphenyl under the action of potassium carbonate to obtain 1'-chloro-8-bromodibenzofuran. Compared with the prior art, thepreparation method can reduce the cost of raw materials and reduce the pollution.

Description

technical field [0001] The present invention relates to the preparation method of 1'-chloro-8-bromodibenzofuran. Background technique [0002] As a display technology with great application prospect, organic electroluminescent device (OLED) has attracted more and more attention. Due to its inherent characteristics, such as self-illumination, wide viewing angle, fast response speed, flexible display and many other advantages, it has become the most favorable competitor for the next generation of display technology. 1'-Chloro-8-bromodibenzofuran can be used as an intermediate of organic light-emitting materials, which has broad application prospects, and the research on its synthesis method is of great significance. [0003] At present, the preparation method of 1'-chloro-8-bromodibenzofuran is reported for the first time by patent KR201841607, which adopts 1-fluoro-2-iodo-3-chlorobenzene and 2-methoxy-5-bromo Phenylboronic acid is used as a raw material, and it is completed...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/91
CPCC07D307/91
Inventor 聂伟文税新凤庞玉东
Owner 安徽秀朗新材料科技有限公司
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