A kind of preparation method of high-purity 3-bromo-9-phenylcarbazole

A technology of phenylcarbazole and aminophenyl, which is applied in the field of preparation of high-purity 3-bromo-9-phenylcarbazole, can solve problems such as difficulty in large-scale production, high cost of raw materials, and harsh reaction conditions, and achieves The effect of avoiding the process of removing dibromine, reducing production costs, and mild reaction conditions

Active Publication Date: 2020-02-21
BEIJING BAYI SPACE LCD MATERIALS TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] However, the various synthetic methods mentioned above either have harsh reaction conditions or high cost of raw materials, making it difficult to achieve large-scale production

Method used

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  • A kind of preparation method of high-purity 3-bromo-9-phenylcarbazole
  • A kind of preparation method of high-purity 3-bromo-9-phenylcarbazole
  • A kind of preparation method of high-purity 3-bromo-9-phenylcarbazole

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Experimental program
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Effect test

Embodiment 1

[0060] This embodiment provides a preparation method of 3-bromo-9-phenylcarbazole, specifically, the method includes the following steps:

[0061] (1) Add 23.59 g of p-dibromobenzene (molecular weight 235.9, 0.1 mol) and 235.9 mL of dichloromethane into a reaction flask equipped with stirring, condenser and thermometer, control the temperature at 30°C, and add concentrated Nitric acid 9.26g (concentration: 68%) (molecular weight: 63, 0.1mol), the reaction was completed after two hours of reaction. Wash the obtained organic phase with water to neutrality, add 10 g of sodium sulfate to dry, and then concentrate to dryness under reduced pressure to obtain 27.52 g of 1,4-dibromo-2-nitrobenzene (molecular weight: 280.9, 0.098 mol); MS (FAB): m / z 280(M+)

[0062] (2) 1,4-dibromo-2-nitrobenzene, 16.58 g of diphenylamine (molecular weight 169.2, 0.098 mol), 0.7 g of cuprous oxide (molecular weight 143.08, 0.0049 mol), 18 - Crown ether-6 1.29g (molecular weight 264.32, 0.0049mol), po...

Embodiment 2

[0068] This embodiment provides a preparation method of 3-bromo-9-phenylcarbazole, specifically, the method includes the following steps:

[0069] (1) Add 23.59 g of p-dibromobenzene (molecular weight 235.9, 0.1 mol) and 353.8 mL of dichloroethane into a reaction flask equipped with stirring, condenser, and thermometer, control the temperature at 25°C, and add concentrated Nitric acid 10.19g (68% content) (molecular weight 63, 0.11mol), the reaction was completed after two hours of reaction. The obtained organic phase was washed with water until neutral, dried by adding 10 g of sodium sulfate, and then concentrated to dryness under reduced pressure to obtain 27.66 g of 1,4-dibromo-2-nitrobenzene (molecular weight: 280.9, 0.098 mol).

[0070] (2) 1,4-dibromo-2-nitrobenzene prepared in step (1), 16.58g of diphenylamine (molecular weight 169.2, 0.098mol), 0.485g of cuprous chloride (molecular weight 98.99, 0.0049mol), 1.29g of 18-crown-6 (molecular weight 264.32, 0.0049mol), 27....

Embodiment 3

[0075] This embodiment provides a preparation method of 3-bromo-9-phenylcarbazole, specifically, the method includes the following steps:

[0076] (1) Add 23.59 g of p-dibromobenzene (molecular weight 235.9, 0.1 mol) and 471.8 mL of chloroform into a reaction flask with stirring, condenser and thermometer, control the temperature at 25 °C, and add concentrated nitric acid 11.1 l g (68% content) (molecular weight 63, 0.12 mol), the reaction ended after two hours of reaction. The obtained organic phase was washed with water until neutral, dried by adding 10 g of sodium sulfate, and then concentrated to dryness under reduced pressure to obtain 27.41 g of 1,4-dibromo-2-nitrobenzene (molecular weight: 280.9, 0.097 mol).

[0077] (2) 1,4-dibromo-2-nitrobenzene, 16.41 g of diphenylamine (molecular weight 169.2, 0.097 mol), 0.69 g of cuprous bromide (molecular weight 143.35, 0.00485 mol), Add 1.28g of 18-crown-6 (molecular weight 264.32, 0.00485mol), cesium carbonate 1.58g (molecular...

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Abstract

The invention discloses a preparation method of high-purity 3-bromine-9-phenylcarbazole, and belongs to the field of synthesis of organic chemicals. The method comprises the following steps: (1) conducting a nitratlon reaction on benzene dibromide to prepare an intermediate, that is, 1,4-dibromo-2-nitrobenzene; (2) enabling 1,4-dibromo-2-nitrobenzene and diphenylamine to have an Ullmann coupling reaction to prepare an intermediate, that is, (4-bromine-2-nitrobenzophenone) diphenylamine; (3) enabling the intermediate, that is, (4-bromine-2-nitrobenzophenone) diphenylamine to have a reduction reaction to prepare an intermediate, that is, (4-bromine-2-aminophenyl) diphenylamine; and (4) enabling the intermediate, that is, (4-bromine-2-aminophenyl) diphenylamine, to have a diazotization ring closing reaction to prepare 3-bromine-9-phenylcarbazole. 3-bromine-9-phenylcarbazole prepared through the method is used in the fields of OLED photoelectric materials, medicines, dyes, pesticides and the like, and is an important carbazole intermediate; the reaction operation is simple, the cost of the raw materials is low, the yield is relatively high, and the quality is high; and moreover, the process of removing dibromo in the traditional preparation method is avoided, and the production convenience is greatly improved.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a preparation method of high-purity 3-bromo-9-phenylcarbazole. Background technique [0002] Carbazole is a typical electron-rich group. The large conjugated π electrons make it have good hole transport ability and high luminescence ability; and because the carbazole group is a large rigid planar structure, the group rigidity is strong, and it can Effectively increase the glass transition temperature of the compound, these inherent properties make the research of carbazole compounds in organic optoelectronic materials widely. Other derivatives prepared from carbazole are also widely used in fields such as OLED optoelectronic materials, medicine, dyes and pesticides. [0003] 3-Bromo-9-phenylcarbazole is an important class of organic chemical intermediates, and other chemical products prepared from it are widely used in the field of optoelectronics, pesticides, medicines...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/88
CPCC07D209/88
Inventor 田会强邓师勇姜天孟戴雄高立龙张海威张强苏学辉
Owner BEIJING BAYI SPACE LCD MATERIALS TECH
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