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Preparation method of 4-bromocarbazole

A technology of bromocarbazole and o-bromophenylboronic acid, which is applied in the field of preparation of 4-bromocarbazole, can solve the problems such as dark color of target product, influence on use effect, etc., so as to improve yield, improve selectivity, and enhance coordination ability Effect

Active Publication Date: 2014-07-23
PUYANG HUICHENG ELECTRONICS MATERIAL +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are few reports on 4-bromocarbazole derivatives, and its synthesis is mainly through nitro ring closure to form a carbazole structure. A method for synthesizing 4-bromocarbazole by reducing the nitro group with a reagent, which produces triphenylphosphine oxide in actual use, which makes the target product darker and affects the use effect

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0019] 15.7 g (0.1 mol) of o-chloronitrobenzene, 20 g (0.1 mol) of o-bromophenylboronic acid, 0.15 g (0.5 mmol) of tris(4-methylphenyl)phosphine and 42.4 g (0.2 mol) of anhydrous potassium phosphate ) into the reaction flask equipped with mechanical stirring, reflux condenser, thermometer and oil bath heating device, then add 200 mL solvent DMSO, and add catalyst tris(dibenzylideneacetone) dipalladium 0.23 g after passing inert gas into the system (0.25 mmol). Heat the reaction at 60-90°C, continue the reaction at constant temperature for 3 h, and then end the reaction. Lower the temperature of the reaction solution below 40 °C, add water to terminate the reaction, extract the organic layer with 200 mL of dichloromethane, separate the liquid, separate the organic layer, dry with 200 g of anhydrous sodium sulfate overnight, concentrate the organic phase to obtain a dark reddish-brown liquid 2 -Bromo-2'-nitrobiphenyl 39 g; under the protection of inert gas, put the reddish-brow...

example 2

[0022] 14.1 g (0.09 mol) of o-chloronitrobenzene, 20 g (0.1 mol) of o-bromophenylboronic acid, 0.3 g (1 mmol) of tris(4-methylphenyl)phosphine and 42.4 g (0.2 mol) of anhydrous potassium phosphate ) into the reaction flask equipped with mechanical stirring, reflux condenser, thermometer and oil bath heating device, then add solvent 200 mL DMSO, add catalyst tris(dibenzylideneacetone) dipalladium 0.46 g after passing inert gas into the system (0.5 mmol). Heat the reaction at 60-90°C, continue the reaction at constant temperature for 3 hours, then add water to the reaction solution to terminate the reaction, extract the organic layer with 200 mL of dichloromethane, separate the organic layer, dry with 200 g of anhydrous sodium sulfate overnight, concentrate the organic phase to obtain a reddish-brown liquid 42 g of 2-bromo-2'-nitrobiphenyl; under the protection of inert gas, put the reddish-brown liquid into the reaction flask equipped with mechanical stirring, thermometer and r...

example 3

[0024] 12.6 g (0.08 mol) of o-chloronitrobenzene, 20 g (0.1 mol) of o-bromophenylboronic acid, 0.21 g (0.7 mmol) of tris(4-methylphenyl)phosphine and 42.4 g (0.2 mol) of anhydrous potassium phosphate ) into the reaction flask equipped with mechanical stirring, reflux condenser, thermometer and oil bath heating device, then add 200 mL solvent DMSO, and add catalyst tris(dibenzylideneacetone) dipalladium 0.32 g after passing inert gas into the system (0.35 mmol). Heat the reaction at 60-90°C, continue the reaction at constant temperature for 3 hours, then add water to the reaction to terminate the reaction, extract the organic layer with 200 mL of dichloromethane, separate the organic layer, dry with 200 g of anhydrous sodium sulfate overnight, concentrate the organic phase to obtain a dark brown liquid 37 g of 2-bromo-2'-nitrobiphenyl; under the protection of inert gas, put the reddish-brown liquid into the reaction flask equipped with mechanical stirring, thermometer and reflu...

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Abstract

The invention discloses a preparation method of 4-bromocarbazole, which belongs to the field of organic chemical synthesis. The method comprises the following steps: by using o-bromophenylboronic acid as a raw material, a DMSO (dimethylsulfoxide) solvent and o-chloronitrobenzene to generate Suzuki reaction in the presence of combined catalysis of palladium metal and an organic phosphine ligand so as to obtain 2-bromine-2'-nitrobiphenyl; and then synthesizing a product 4-bromocarbazole, from 2-bromine-2'-nitrobiphenyl by using triphenyl phosphite as a reductant. During reaction, side reactions are few, the method is simple to operate and the yield is high. The synthesized 4-bromocarbazole can be used in the fields of organic photoelectric materials, medicines and the like, and is an important intermediate for carbazole photoelectric materials, medicines and presides.

Description

technical field [0001] The invention relates to a preparation method of 4-bromocarbazole, which belongs to the field of organic chemical synthesis. Background technique [0002] Carbazole and its derivatives are a class of heterocyclic aromatic compounds with large π-electron conjugated systems and strong intramolecular electron transfer properties. From the structural point of view, the electrophilic N atom of carbazole absorbs double atoms through the inductive effect. The electrons on the bond; on the other hand, due to the p-π conjugation effect, the unshared electrons of the N atom are supplied to the double bond, making the double bond rich in electrons. Therefore, the carbazole ring has a strong hole transport ability, and the carbazole polymer or small molecule compound can be used as a hole transport layer in organic electroluminescent devices, which reduces the crystallization of small molecule materials and improves the device life. At the same time, the opportun...

Claims

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Application Information

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IPC IPC(8): C07D209/88
CPCC07D209/88
Inventor 杨振强蒋卫鹏杨瑞娜屈凤波孙敏青李奎刘铁良马伟
Owner PUYANG HUICHENG ELECTRONICS MATERIAL
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