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Preparation method of indolo [2, 3-A] carbazole

A technology of 3-A and indole, which is applied in the chemical field, can solve the problems of unfavorable mass production, prominent environmental protection problems, high cost, etc., and achieve the improvement of oxidation addition and metallization exchange rate, low production cost and good product quality Effect

Active Publication Date: 2021-01-22
SINOSTEEL NANJING NEW MATERIALS RES INST CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] Aiming at the problems of the existing methods for synthesizing indolo[2,3-A]carbazole with low yield, high cost, prominent environmental protection problems and unfavorable industrial mass production, the present invention provides an indolo[2,3-A] -A]carbazole preparation method, by optimizing the synthesis route, a new synthesis method of indolo[2,3-A]carbazole with mild reaction conditions, high efficiency and good economy is obtained

Method used

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  • Preparation method of indolo [2, 3-A] carbazole
  • Preparation method of indolo [2, 3-A] carbazole
  • Preparation method of indolo [2, 3-A] carbazole

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Experimental program
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Embodiment 1

[0042]Under nitrogen protection, add 357.6g o-dibromobenzene (99%, 1.5mol), 16.4g o-phenylenediamine (99%, 0.15mol), 0.35g tris(dibenzylideneacetone) dipalladium in a 500mL reaction flask (99%, 0.375mmol), 1.45g cuprous iodide (99%, 7.5mmol), 0.76g10% tri-tert-butylphosphine pentane solution (10%in Pentane, 0.375mmol), 91.8g triethylamine (99 %, 0.9mol), feeding is completed, the temperature is raised to 130°C, the stirring speed is 600rpm, and the heat preservation reaction is carried out for 24hr. After the reaction is completed, the unreacted o-dibromobenzene is recovered by distillation under reduced pressure, and water and 2-methyltetrahydrofuran are added to the residue to extract , the crude product obtained by precipitation of the organic layer was crystallized from a tetrahydrofuran / ethanol mixed solvent (1:1 by volume) to obtain 34.6 g of indolo[2,3-A]carbazole, with a content of 99.1% and a yield of 89.3%.

[0043] Such as figure 1 Shown is the present embodiment p...

Embodiment 2

[0045] Under nitrogen protection, add 357.6g o-dibromobenzene (99%, 1.5mol), 16.4g o-phenylenediamine (99%, 0.15mol), 0.084g palladium acetate (99%, 0.375mmol) in the 500mL reaction flask, 2.18g cuprous bromide (99%, 15mmol), 0.18g 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl (99%, 0.375mmol), 116.4g sodium tert-butoxide (99 %, 1.2mol), feeding is completed, the temperature is raised to 110°C, the stirring speed is 600rpm, and the heat preservation reaction is carried out for 24hr. After the reaction is completed, the unreacted o-dibromobenzene is recovered by distillation under reduced pressure, and water and 2-methyltetrahydrofuran are added to the residue to extract , the crude product obtained by precipitation of the organic layer was crystallized with tetrahydrofuran / ethanol mixed solvent (volume ratio 1:1) to obtain 35.4 g of indolo[2,3-A]carbazole with a content of 99.3% and a yield of 91.6%.

Embodiment 3

[0047] Under nitrogen protection, add 715.2g o-dibromobenzene (99%, 3mol), 16.4g o-phenylenediamine (99%, 0.15mol), 0.17g palladium acetate (99%, 0.75mmol), 1.02g in 1L reaction flask g copper chloride (99%, 7.5mmol), 0.27g n-butyl two (1-adamantyl) phosphine (99%, 0.75mmol), 116.4g potassium tert-butoxide (99%, 1.2mol), feed intake complete , the temperature was raised to 110°C, the stirring speed was 600rpm, and the heat preservation reaction was carried out for 48 hours. After the reaction, the unreacted o-dibromobenzene was recovered by distillation under reduced pressure, water and 2-methyltetrahydrofuran were added to the residue for extraction, and the organic layer was desolvated to obtain the crude product as 28.5 g of indolo[2,3-A]carbazole was crystallized from a tetrahydrofuran / ethanol mixed solvent (volume ratio 1:1), with a content of 99.0% and a yield of 73.5%.

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Abstract

The invention discloses a preparation method of indolo [2, 3-A] carbazole, which belongs to the technical field of chemistry. The preparation method comprises the following steps of carrying out C-N coupling and C-C coupling cascade reaction on o-dibromobenzene and o-phenylenediamine under the action of a catalyst, a ligand and alkali to obtain indolo [2, 3-A] carbazole, wherein the catalysts area palladium salt catalyst and a copper salt catalyst, the palladium salt catalyst comprises palladium chloride, palladium acetate, tetra(triphenylphosphine) palladium, palladium trifluoroacetate, palladium acetylacetonate or tri(dibenzylideneacetone) dipalladium, and the copper salt catalyst comprises cuprous iodide, cuprous chloride, cuprous bromide, cuprous oxide, copper sulfate, copper chloride, copper acetate or copper trifluoroacetate, the ligand is a phosphine ligand, and the alkali is organic alkali or inorganic alkali. According to the method, o-phenylenediamine and o-dibromobenzene which are cheap and easily available are used as raw materials, and compared with the prior art, the method has the advantages of short reaction steps, easily available raw materials, low production cost, environmental friendliness and the like.

Description

technical field [0001] The invention relates to the technical field of chemistry, in particular to a preparation method of indolo[2,3-A]carbazole. Background technique [0002] OLED, or Organic Light-Emitting Diode (Organic Light-Emitting Diode), is an organic electroluminescent device with a multilayer structure, which can be applied to the field of display and lighting. Electroluminescent third-generation display technology. As a new display technology, OLED is currently in the early stage of the industry explosion. According to the development history of display technology, the next ten years may be an era in which OLED will gradually dominate. Indolo[2,3-A]carbazole is an important intermediate in the synthesis of organic optoelectronic materials. Therefore, research on the synthesis of indolo[2,3-A]carbazole is of great significance for the development of OLED industry. [0003] According to literature reports, indolo[2,3-A]carbazole mainly has the following several s...

Claims

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Application Information

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IPC IPC(8): C07D487/04B01J31/30
CPCC07D487/04B01J27/122B01J31/30
Inventor 朱叶峰裴晓东杨修光吴忠凯张玲骆艳华
Owner SINOSTEEL NANJING NEW MATERIALS RES INST CO LTD
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