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Preparation method of carbazole ring-containing compound

A technology of compounds and carbazole rings, which is applied in the field of preparation of compounds containing carbazole rings, can solve the problems of long reaction time, dangerous solid waste, troublesome disposal, etc., achieve easy post-processing, reduce reaction temperature and reaction time, The effect of reducing dosage

Active Publication Date: 2020-04-21
FUYANG XINYIHUA MATERIAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] (1) A large amount of triphenylphosphine oxide is produced as a by-product, which is a dangerous solid waste and troublesome to deal with
(2) Refluxing reaction is required in o-dichlorobenzene, the temperature is higher and the reaction time is longer

Method used

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  • Preparation method of carbazole ring-containing compound
  • Preparation method of carbazole ring-containing compound
  • Preparation method of carbazole ring-containing compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] In this embodiment, the preparation method of 2-fluorocarbazole is provided, and the reaction formula is as follows:

[0043]

[0044] In a 100ml three-necked flask, add 50ml o-dichlorobenzene, 2.17g (0.01mol) 4-fluoro-2-nitro-1,1'-biphenyl, 2.62g (0.01mol) triphenylphosphine, 1.12g (0.02mol) iron powder was heated to 177°C and refluxed for 20 hours, filtered while it was hot, the mother liquor was concentrated to dryness under reduced pressure, the obtained solid was ground, washed with methanol, and filtered to remove methanol, the obtained solid silica gel column chromatography was separated , sherwood oil: ethyl acetate: dichloromethane=8:1:1 (volume ratio) elution, obtains product 2-fluorocarbazole 1.70 grams, yield 91.9%, the product is carried out with the solariX XR mass spectrometer that BRUKER produces Detect and determine that the product molecular weight is 185.

Embodiment 2

[0046] Compared with Example 1, the only difference is that after adding iron powder, the reaction temperature was kept at 110°C for 20 hours to obtain 1.71 grams of product 2-fluorocarbazole, with a yield of 92.4%. The product was detected by solariX XR produced by BRUKER , determine that the product molecular weight is 185.

Embodiment 3

[0048] Compared with Example 1, the only difference is that the reaction solvent was changed to toluene, and the reaction temperature was kept at 106°C for 10 hours to obtain 1.75 grams of product 2-fluorocarbazole, with a yield of 94.6%, using solariX XR produced by BRUKER The product is detected to determine that the molecular weight of the product is 185.

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Abstract

The invention provides a preparation method of a carbazole ring-containing compound, comprising the following step: a compound shown as a formula I-1 is subjected to a reaction in an organic solvent in the presence of metal and / or metal salt by using triphenylphosphine as a reducing agent to generate a compound shown as the formula I. In the invention, the carbazole ring compound is prepared by taking triphenylphosphine as a reducing agent and utilizing a nitro compound to react under the cooperation of the co-reducing agent, so that the dosage of triphenylphosphine is reduced, the generationamount of dangerous solid wastes is reduced, the post-treatment is easy, and the reaction temperature can be greatly reduced and the reaction time can be greatly shortened while high product yield isensured.

Description

technical field [0001] The invention belongs to the technical field of organic material synthesis, and relates to a preparation method of compounds containing carbazole rings. Background technique [0002] Organic compounds containing carbazole rings, as an important intermediate, are widely used in medicine, pesticides and organic electronic materials. [0003] Some preparation methods of carbazole ring compounds have been disclosed in the prior art. For example, US2013 / 303524 discloses that in o-dichlorobenzene, the raw material reacts with triphenyl o to generate 2-fluorocarbazole. The reaction formula as follows: [0004] [0005] But the reaction temperature is as high as 175°C, the reaction time is 8 hours, and the reaction yield is 89%. [0006] The following reaction is disclosed in CN104447505: [0007] [0008] In this reaction, the raw material and triethyl phosphite were refluxed in toluene for 10 hours to prepare 2-phenylcarbazole with a yield of 77%. ...

Claims

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Application Information

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IPC IPC(8): C07D209/88C07D209/86C07D487/04C07D209/80
CPCC07D209/80C07D209/86C07D209/88C07D487/04
Inventor 王占奇丁言苏郭林林李志强
Owner FUYANG XINYIHUA MATERIAL TECH
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