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A kind of preparation method of 4-bromocarbazole

A technology of bromocarbazole and o-bromoaniline, applied in the field of chemistry, can solve problems such as unfavorable mass production, high cost, outstanding environmental protection problems, etc., and achieve the effects of simple structure, low production cost and good product quality

Active Publication Date: 2021-11-02
SINOSTEEL NANJING NEW MATERIALS RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0016] Aiming at the problems that the existing method for synthesizing 4-bromocarbazole is high in cost, prominent in environmental protection, and unfavorable for industrialized mass production, the present invention provides a method for preparing 4-bromocarbazole. By optimizing the synthesis route, a reaction condition is obtained A new method for the synthesis of 4-bromocarbazole with mildness, high efficiency and good economy

Method used

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  • A kind of preparation method of 4-bromocarbazole
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  • A kind of preparation method of 4-bromocarbazole

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Embodiment 1

[0042]Under nitrogen protection, add 357.6g m-dibromobenzene (99%, 1.5mol), 26.1g o-bromoaniline (99%, 0.15mol), 0.35g three (dibenzylidene acetone) dipalladium ( 99%, 0.375mmol), 0.76g10% tri-tert-butylphosphine pentane solution (10%in Pentane, 0.375mmol), 61.2g triethylamine (99%, 0.6mol), after feeding, the temperature was raised to 150°C and stirred The rotation speed was 600rpm, and the heat preservation reaction was carried out for 24hr. After the reaction was completed, the unreacted m-dibromobenzene was recovered by distillation under reduced pressure, and water and ethyl acetate were added to the residue for extraction. Azole, content 99.5%, yield 89.3%.

Embodiment 2

[0044] Under nitrogen protection, add 357.6g m-dibromobenzene (99%, 1.5mol), 26.1g o-bromoaniline (99%, 0.15mol), 0.084g palladium acetate (99%, 0.375mmol), 0.18g in a 500mL reaction flask g 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl (99%, 0.375mmol), 58.2g sodium tert-butoxide (99%, 0.6mol), after feeding, the temperature was raised to 130°C, The stirring speed was 600rpm, and the heat preservation reaction was carried out for 24 hours. After the reaction, the unreacted m-dibromobenzene was recovered by distillation under reduced pressure. Water and ethyl acetate were added to the residue for extraction. Carbazole, content 99.6%, yield 92.5%.

Embodiment 3

[0046] Under nitrogen protection, add 715.2g m-dibromobenzene (99%, 3mol), 26.1g o-bromoaniline (99%, 0.15mol), 0.17g palladium acetate (99%, 0.75mmol), 0.27g in 1L reaction flask n-Butylbis(1-adamantyl)phosphine (99%, 0.75mmol), 67.9g potassium tert-butoxide (99%, 0.6mol), after feeding, the temperature was raised to 110°C, the stirring speed was 600rpm, and the reaction was kept for 48hr. After the reaction, the unreacted m-dibromobenzene was recovered by distillation under reduced pressure, water and ethyl acetate were added to the residue for extraction, the organic layer was desolvated to obtain the crude product, and crystallized with ethanol to obtain 30.0 g of 4-bromocarbazole, the content of which was 99.1%. The rate is 80.5%.

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Abstract

The invention discloses a preparation method of 4-bromocarbazole, which belongs to the technical field of chemistry. A kind of preparation method of 4-bromocarbazole, under the action of catalyst, ligand and alkali, o-bromoaniline and m-dibromobenzene undergo C-N coupling and C-C coupling series reaction, one-pot method and one-step synthesis 4-bromocarbazole, wherein, the m-dibromobenzene is both a reactant and simultaneously dibromobenzene is also used as a reaction solvent, and the remaining m-dibromobenzene can be reclaimed after the reaction finishes. The preparation method of the present invention uses cheap and easy-to-obtain o-bromoaniline and m-dibromobenzene as raw materials, and obtains the product 4-bromocarbazole in one step through a one-pot series reaction. Compared with the prior art, it avoids the reduction of the nitro group into a ring steps, that is, the reaction steps are shortened, which has the advantages of low production cost and environmental friendliness.

Description

technical field [0001] The invention relates to the technical field of chemistry, in particular to a preparation method of 4-bromocarbazole. Background technique [0002] Carbazole and its derivatives are a class of heterocyclic aromatic compounds with large π-electron conjugated system and strong intramolecular electron transfer characteristics. From the structural point of view, the electrophilic nitrogen atom of carbazole absorbs double On the other hand, due to the p-π conjugation effect, the unshared electrons of the nitrogen atom donate to the double bond, making the double bond rich in electrons. Therefore, the carbazole ring has a strong hole transport ability, and the carbazole polymerization Objects or small molecular compounds can be used as hole transport layers in organic electroluminescent devices, which reduces the crystallization of small molecular materials and improves the life of the device. At the same time, it increases the chance of electron-hole recomb...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/88
CPCC07D209/88
Inventor 朱叶峰裴晓东杨修光张玲吴忠凯骆艳华
Owner SINOSTEEL NANJING NEW MATERIALS RES INST CO LTD
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