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Controllable preparation method of carbazole bromo-compound

A compound, the technology of carbazole bromide, which is applied in the field of controllable preparation of carbazole bromide compounds, achieves the effects of high yield, mild reaction conditions and easy realization

Inactive Publication Date: 2014-05-07
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, a milder, more controllable, and isolated bromination method has not been reported in the literature

Method used

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  • Controllable preparation method of carbazole bromo-compound
  • Controllable preparation method of carbazole bromo-compound
  • Controllable preparation method of carbazole bromo-compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Using carbazole as the starting material, react with N-bromosuccinimide to synthesize 1,3,6,8-tetrabromocarbazole compound:

[0031]

[0032] Reaction Scheme

[0033]

[0034] Step 1: Under a nitrogen atmosphere, add 5 g (29.94 mmol) of carbazole and 15 mL of N,N-diformamide to a three-necked flask equipped with magnetic stirring. After the carbazole is completely dissolved, the prepared concentration is 1.996 mol / For solution A of L, reduce the reaction system to 5°C with an ice-water bath; N-bromosuccinimide (21.317 g, 119.76 mmol) was dissolved in 100 mL N,N-diformamide to prepare a concentration of 1.1976 mol / L solution B, the ratio of the amount of N,N-diformamide in solution B to the amount of N,N-diformamide in solution A is 20:3;

[0035] Step 2: Control the reaction temperature at 5°C, slowly add solution B to solution A slowly with a constant pressure funnel;

[0036] Step 3: After the dropwise addition, react at room temperature for 10 hours;

[00...

Embodiment 2

[0040] Using carbazole as the starting material, react with N-bromosuccinimide to synthesize 1,3,6-tribromocarbazole:

[0041]

[0042] Reaction Scheme

[0043]

[0044] Step 1: Under a nitrogen atmosphere, add 5 g (29.94 mmol) of carbazole and 15 mL of N,N-diformamide to a three-necked flask equipped with magnetic stirring. After the carbazole is completely dissolved, the prepared concentration is 1.996 mol / For solution A of L, the reaction system was lowered to 3°C with an ice-water bath; N-bromosuccinimide (15.898 g, 89.82 mmol) was dissolved in 100 mL N,N-diformamide to prepare a concentration of 0.8932 mol / L solution B, the ratio of the amount of N,N-diformamide in solution B to the amount of N,N-diformamide in solution A is 20:3;

[0045] Step 2: Control the reaction temperature at 3°C, and slowly add solution B to solution A dropwise with a constant pressure funnel;

[0046] Step 3: After the dropwise addition, react at room temperature for 10 hours;

[0047] S...

Embodiment 3

[0051] Using carbazole as the starting material, react with N-bromosuccinimide to synthesize 3,6-dibromocarbazole:

[0052]

[0053] Scheme of the reaction scheme:

[0054]

[0055] Step 1: Under a nitrogen atmosphere, add 5 g (29.94 mmol) of carbazole and 15 mL of N,N-diformamide to a three-necked flask equipped with magnetic stirring. After the carbazole is completely dissolved, the prepared concentration is 1.996 mol / For solution A of L, reduce the reaction system to 0°C with an ice-water bath; N-bromosuccinimide (10.601 g, 59.84 mmol) was dissolved in 60 mL N,N-diformamide to prepare a concentration of 0.9973 mol / L solution B, the ratio of the amount of N,N-diformamide in solution B to the amount of N,N-diformamide in solution A is 4:1;

[0056] Step 2: Control the reaction temperature at 0°C, and slowly add solution B to solution A slowly with a constant pressure funnel;

[0057] Step 3: After the dropwise addition, react at room temperature for 10 hours;

[00...

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Abstract

The invention provides a controllable preparation method of a carbazole bromo-compound. The controllable preparation method is conducted in the nitrogen atmosphere and comprises the following steps of: (1) dissolving the carbazole in N, N-dimethyl amide, and preparing solution A with the concentration being 1.996mol / L; dissolving N-bromosuccinimide in the N, N-dimethyl amide, and preparing solution B with the concentration being 1.1976mol / L, wherein the ratio between the used amount of the N, N-dimethyl amide in the solution B and the used amount of the N, N-dimethyl amide in the solution A is 20:3; (2) controlling the reaction temperature to be 5 DEG C, and slowly dripping the solution B into the solution A; (3) after the dripping is finished, reacting for 10 hours under the room temperature; (4) pouring into distilled water, generating white precipitates immediately, filtering the white precipitates, washing the precipitates for three times and drying at the temperature of 1000 DEG C to obtain a primary product; and (5) using dichloromethane to carry out recrystallization and purify the primary product in the step (4) and obtaining 1, 3, 6, 8-tetrabromo carbazole. The controllable preparation method provided by the invention has the advantages of mild reaction condition with easy implementation, high yield, easy separation and purification of the product, no toxicity and harm, no pollutant emission and environmentally friendly and energy-saving effects.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and in particular relates to a controllable preparation method for preparing carbazole brominated compounds. Background technique [0002] The development of material science has driven the progress of society, and a comprehensive view of history has confirmed this point. Human society has entered the Stone Age, Bronze Age, Iron Age, steam engine age, and today's information and computer age from the primitive society of raw hair and blood. It is the emergence of new materials that has caused great changes in history. With the improvement of living standards, people's needs are constantly expanding, and traditional inorganic materials are increasingly unable to meet people's needs. Under this background, people turn their attention to organic materials. Organic materials, also known as organic functional materials, can be manipulated at the molecular level because their properties are easy to contr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/88
CPCC07D209/88
Inventor 叶尚辉周舟胡天庆黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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