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A method for synthesizing 9,9'-diphenyl-3,3'-bicarbazole in one step

A biphenyl and bicarbazole technology, applied in the field of chemical synthesis, can solve the problems of low cost performance and long synthesis process, and achieve the effects of improving conversion rate, simple post-processing, and simplifying the preparation process

Active Publication Date: 2021-05-11
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In order to solve many problems in the synthesis of 9,9′-diphenyl-3,3′-bicarbazole by the traditional palladium-catalyzed method, such as long synthesis process and low cost performance, we have developed a 9,9′-diphenyl-3,3′-bicarbazole catalyzed by Eaton reagent. One-step synthesis of diphenyl-3,3'-bicarbazole

Method used

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  • A method for synthesizing 9,9'-diphenyl-3,3'-bicarbazole in one step
  • A method for synthesizing 9,9'-diphenyl-3,3'-bicarbazole in one step
  • A method for synthesizing 9,9'-diphenyl-3,3'-bicarbazole in one step

Examples

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Effect test

Embodiment 1

[0031] Example 1: One-step method for synthesizing 9,9'-diphenyl-3,3'-bicarbazole, the specific method and steps are:

[0032] (1) Under nitrogen atmosphere, place 1.5g (6.2mmol) 9-phenyl-carbazole in a 50mL round-bottomed flask and raise the temperature to 90°C, heat and stir until melting, and within 5 minutes, 0.78mL or 0.31mmol Eaton The reagent was slowly added dropwise, and the solution turned from colorless to dark brown.

[0033] (2) After continuing to react for 12 hours, 10 mL of methanol was added to continue stirring for 2 hours to quench the reaction. The reactant was diluted with dichloromethane and dried with an appropriate amount of magnesium sulfate. Column chromatography was performed using a mixed solvent of petroleum ether and dichloromethane at a volume ratio of 20:1 as an eluent to obtain a white product with a yield of 46%.

[0034] (3) Unreacted raw materials are recovered and reused, and the comprehensive yield of multiple reactions can reach 70%.

Embodiment 2

[0035] Example 2: One-step method for synthesizing 9,9'-diphenyl-3,3'-bicarbazole, the specific method and steps are:

[0036] (1) Under nitrogen atmosphere, place 1.5g (6.2mmol) 9-phenyl-carbazole in a 50mL round-bottomed flask and heat up to 120°C, heat and stir until melting, and within 5 minutes, 0.78mL or 0.31mmol Eaton The reagent was slowly added dropwise, and the solution turned from colorless to dark brown.

[0037] (2) After continuing to react for 12 hours, 10 mL of methanol was added to continue stirring for 2 hours to quench the reaction. The reactant was diluted with dichloromethane and dried with an appropriate amount of magnesium sulfate. Column chromatography was performed using a mixed solvent of petroleum ether and dichloromethane at a volume ratio of 10:1 as an eluent to obtain a white product with a yield of 44%.

[0038] (3) Unreacted raw materials are recovered and reused, and the comprehensive yield of multiple reactions can reach 68%.

Embodiment 3

[0039] Example 3: One-step method for synthesizing 9,9'-diphenyl-3,3'-bicarbazole, the specific method and steps are:

[0040] (1) Under a nitrogen atmosphere, place 1.5g (6.2mmol) 9-phenyl-carbazole in a 50mL round bottom flask and heat up to 110°C, heat and stir until melted, and within 5 minutes, 1.5mL, 0.62mmol Eaton The reagent was slowly added dropwise, and the solution turned from colorless to dark brown.

[0041] (2) After continuing to react for 12 hours, 10 mL of methanol was added to continue stirring for 2 hours to quench the reaction. The reactant was diluted with dichloromethane and dried with an appropriate amount of magnesium sulfate. Column chromatography was performed using a mixed solvent of petroleum ether and dichloromethane at a volume ratio of 3:1 as an eluent to obtain a white product with a yield of 43%.

[0042] (3) Unreacted raw materials are recovered and reused, and the comprehensive yield of multiple reactions can reach 65%.

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Abstract

The present invention relates to a method for synthesizing 9,9'-diphenyl-3,3'-bicarbazole in one step, comprising the following steps: S01 under a nitrogen atmosphere, heating and stirring 9-phenyl-carbazole to Melt, slowly add Eaton's reagent drop by drop until the solution turns from colorless to dark brown; S02 reaction is completed, add quenching agent and stir to quench the reaction; S03 reactant is diluted with dichloromethane and dried with appropriate amount of magnesium sulfate and dichloromethane mixed solvent as eluent for column chromatography to obtain a white product. The method is catalyzed by Eaton reagent, and the 9-phenyl-3-carbazole is directly coupled to obtain a product by activating the 3-position of carbazole, which shortens the reaction cycle, simplifies the complicated treatment process, and reduces environmental pollution.

Description

technical field [0001] The invention relates to a synthesis method of chemicals, in particular to a synthesis method of 9,9'-diphenyl-3,3'-bicarbazole. Background technique [0002] Over the past three decades, breakthroughs have been achieved in metal-catalyzed coupling represented by C–C coupling. The 2010 Nobel Prize in Chemistry was awarded to E.Negishi, R.Heck, and A.Suzuki in recognition of their outstanding contributions in carbon C-C direct coupling. However, these metal catalysts also have many shortcomings. For example, many by-products will be generated in the reaction catalyzed by organometallic catalysts. At the same time, the high cost and high toxicity of noble metal catalysts also limit their application range. Therefore, it is of great significance to develop a method that does not contain noble metal catalysts, has relatively mild reaction conditions and simple post-treatment. [0003] 9,9'-diphenyl-3,3'-bicarbazole and its derivatives are the star units ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/86
CPCC07D209/86
Inventor 陈润锋袁杰黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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