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Preparation method of 3-bromine-N-phenylcarbazole

A technology of phenylcarbazole and bromocarbazole, which is applied in the field of preparation of 3-bromo-N-phenylcarbazole, can solve the problem of low reaction yield and achieve simple and easy-to-obtain raw materials, simple and easy-to-control reaction process, The effect of short preparation cycle

Active Publication Date: 2021-10-08
山东瑞辰新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method then has the problem that the reaction yield is not high, and the general single-step yield is only 50-60%.

Method used

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  • Preparation method of 3-bromine-N-phenylcarbazole

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Preparation of 3-bromo-N-phenylcarbazole

[0026] (1) Preparation of 2-bromophenylaniline

[0027] Take a 3L four-neck bottle, add 1000ml of dichloromethane I; under stirring, add 200g (1.18mol) of diphenylamine; after dissolving, cool the reaction system to -10~0°C; 580ml of dichloromethane II, and then dropwise added to the diphenylamine solution, the temperature of the reaction system was -9°C when the dropwise addition started. During the dropping process, the temperature of the reaction system should be controlled at a maximum temperature of -1°C; after the dropwise addition, raise the reaction solution to 20-30°C, and after 0.5 hours, TLC monitors that the reaction of diphenylamine is complete; after the reaction, add 1000ml of saturated saline to wash the reaction solution; After liquid separation, the organic phase was dried with anhydrous sodium sulfate. The organic phase was subtracted and evaporated to dryness to obtain 286.7 g of 2-bromophenylaniline, with...

Embodiment 2

[0040] Preparation of 3-bromo-N-phenylcarbazole

[0041] (1) Preparation of 2-bromophenylaniline

[0042] Add 5L of dichloromethane I into a 20L glass kettle; under stirring, add 1000g (5.91mol) of diphenylamine; after dissolving, cool the reaction system to -10~0°C; L dichloromethane II, and then dropwise added to the diphenylamine solution, the temperature of the reaction system was -8.8°C when the dropwise addition started. The maximum temperature of the reaction system during the dropping process is -0.6°C; after the dropwise addition is completed, the reaction solution is raised to 22-24°C, and after 0.5 hours TLC monitors that the reaction of diphenylamine is complete; after the reaction, add 5L of saturated saline to wash the reaction solution; After liquid separation, the organic phase was dried with anhydrous sodium sulfate. The organic phase was subtracted and evaporated to dryness to obtain 1419.3 g of 2-bromophenylaniline, with a yield of 96.8%.

[0043] (2) Pre...

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Abstract

The invention relates to a preparation method of 3-bromine-N-phenylcarbazole, and belongs to the technical field of organic chemistry. The preparation method comprises the steps of by taking diphenylamine as an initial raw material, carrying out bromination reaction to obtain 2-bromophenylaniline; then carrying out intramolecular cyclization to obtain carbazole; then carrying out bromination reaction to obtain 3-bromocarbazole; and finally, carrying out substitution to obtain the 3-bromine-N-phenylcarbazole. By controlling the concentration of reactants and the reaction environment, the selectivity of reaction sites is effectively improved, the used raw materials are simple and easy to obtain, the preparation period is relatively short, and the reaction process is simple and easy to control.

Description

technical field [0001] The invention relates to the technical field of organic chemistry, in particular to a preparation method of 3-bromo-N-phenylcarbazole. Background technique [0002] 3-Bromo-N-phenylcarbazole is an important intermediate in the synthesis of optoelectronic materials, and can synthesize a series of organic electroluminescent materials with macromolecules containing phenylcarbazole groups. There are two main methods for preparing 3-bromo-N-phenylcarbazole in the prior art. One is to use carbazole as a raw material, first pass bromination reaction, and then react with halobenzene through C-N coupling reaction to obtain the target product . This method uses NBS as a brominating agent during bromination, but a small amount of isomers and disubstituted products will be produced during the bromination process, which are difficult to remove in subsequent production and affect the purity of subsequent products. The other is to carry out the C-N coupling reactio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/88
CPCC07D209/88
Inventor 陈丽娟李涛蒋伟光
Owner 山东瑞辰新材料有限公司