Preparation method of N-phenyl-3-bromocarbazole

A technology of bromocarbazole and phenyl, which is applied in the field of organic compound synthesis and achieves the effects of convenient industrial production, high yield and low reaction temperature

Inactive Publication Date: 2014-02-26
DALIAN NETCHEM CHIRAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above method iodobenzene and palladium catalysts are expensive, and the reaction temperature is high. In the reaction of N-phenylcarbazole and NBS bromination, the polarity of the monosubstituted product and the disubstituted impurity are similar and difficult to separate. It needs to be purified by column chromatography, and the operation is cumbersome.

Method used

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  • Preparation method of N-phenyl-3-bromocarbazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] A kind of preparation method of N-phenyl-3-bromocarbazole, comprises following two steps:

[0026] The preparation of the first step 3-bromocarbazole:

[0027] Add 50.14 g (0.30 mol) of carbazole to a 500 mL four-neck flask equipped with magnetic stirring and a thermometer, add 200 mL of ethyl acetate and stir at room temperature to dissolve, slowly add 100 mL of ethyl acetate to dissolve 53.43 g (0.30mol) N-bromosuccinimide (NBS), react for 2 to 4 hours after dropping, control in TLC until the reaction is complete, filter, wash with 40% aqueous sodium hydroxide solution, separate liquid, keep the organic layer, evaporate The organic solvent was removed to obtain 69.42 g of solid, the crude product yield was 94.25%, recrystallized from ethanol, filtered and dried to obtain 52.04 g of 3-bromocarbazole, and the recrystallized yield was 74.96%.

[0028] The preparation of the second step N-phenyl-3-bromocarbazole:

[0029] Add 52.04g (0.21mol) of 3-bromocarbazole, 32.76g...

Embodiment 2

[0031] A kind of preparation method of N-phenyl-3-bromocarbazole, comprises following two steps:

[0032] The preparation of the first step 3-bromocarbazole:

[0033] Add 49.94 g (0.30 mol) of carbazole to a 500 mL four-neck flask equipped with a magnetic stirrer and a thermometer, add 200 mL of ethyl acetate and stir at room temperature to dissolve, lower the temperature to 0°C and slowly add 100 mL of ethyl acetate to dissolve while stirring 69.38g (0.39mol) of NBS, reacted for 2 to 4 hours after dropping, controlled by TLC until the end of the reaction, filtered, washed with 40% aqueous sodium hydroxide solution, separated, kept the organic layer, and evaporated the organic solvent to obtain 71.38g of solid , the yield of crude product was 96.73%, recrystallized from ethanol, filtered and dried to obtain 57.78g of 3-bromocarbazole, and the yield of recrystallized was 80.96%.

[0034] The preparation of the second step N-phenyl-3-bromocarbazole:

[0035] Add 57.78g (0.235m...

Embodiment 3

[0037] A kind of preparation method of N-phenyl-3-bromocarbazole, comprises following two steps:

[0038] The preparation of the first step 3-bromocarbazole:

[0039] Add 50.04 g (0.30 mol) of carbazole to a 500 mL four-neck flask equipped with a magnetic stirrer and a thermometer, add 200 mL of ethyl acetate and stir at room temperature to dissolve, lower the temperature to 0°C and slowly add 100 mL of ethyl acetate to dissolve while stirring 47.94 g (0.30mol) of bromine, reacted for 2 to 4 hours after dropping, controlled in TLC until the end of the reaction, filtered, washed with 40% aqueous sodium hydroxide solution, separated, kept the organic layer, and evaporated the organic solvent to obtain a solid 68.92 g, the crude product yield was 94.05%, recrystallized from ethanol, filtered and dried to obtain 54.04 g of 3-bromocarbazole, and the recrystallized yield was 77.06%.

[0040] The preparation of the second step N-phenyl-3-bromocarbazole:

[0041] Add 54.04 g (0.22 m...

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Abstract

The invention belongs to the field of organic compound synthesis and provides a preparation method of N-phenyl-3-bromocarbazole. The preparation method comprises the following two steps: 1. with carbazole as a raw material, reacting with N-bromosuccinimide in ethyl acetate to obtain 3-bromocarbazole; and 2. then mixing 3-bromocarbazole, bromobenzene, potassium carbonate and a copper salt catalyst, adding the solvents such as DMF (dimethylformamide) or methylbenzene or dimethylbenzene to react at 80-150 DEG C under the protection of nitrogen to generate the N-phenyl-3-bromocarbazole. The preparation method has the beneficial effects that the raw materials such as carbazole, bromobenzene and the copper salt catalyst are economical and accessible and convenient to directly purchase from the markets; the preparation method is simple, is convenient to operate, is high in yield and lower in cost and is convenient for industrial production.

Description

Technical field: [0001] The invention belongs to the field of organic compound synthesis and relates to a preparation method of N-phenyl-3-bromocarbazole. Background technique: [0002] Carbazole derivatives are typical electron-rich groups, so carbazole derivatives have good hole transport ability and high luminescence ability, and because of their large rigid planar structure, group movement is difficult, which can effectively improve the Glass transition temperature (Tg). Therefore, carbazole derivatives are a class of materials with high Tg, high luminous intensity and good hole transport properties, and can be used as hole transport materials and luminescent materials. [0003] N-phenyl-3-bromocarbazole is an important chemical intermediate that can be further synthesized into organic optoelectronic materials, which have been widely used in organic light-emitting diodes (OL ED). [0004] The currently known synthesis method of N-phenyl-3-bromocarbazole: use carbazo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/88
CPCC07D209/88
Inventor 李欣郑鹏
Owner DALIAN NETCHEM CHIRAL TECH
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