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Preparation method of 3-(1-adamantyl) carbazole

A technology of adamantyl and carbazole, which is applied in the field of preparation of 3-carbazole, can solve problems such as imperfect production methods, and achieve the effect of simple reaction operation process and post-treatment

Pending Publication Date: 2021-09-03
山东盛安贝新能源有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

After literature research, we found that carbazoles with a large rigid structure of adamantyl groups have not been reported yet. The adamantyl group belongs to a polycyclic cage structure and has a stable molecular structure, which is more in line with the structural characteristics of OLED materials. However, the specific production method is not yet known. Complete

Method used

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  • Preparation method of 3-(1-adamantyl) carbazole

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] A kind of preparation method of 3-(1-adamantyl) carbazole, comprises the following steps:

[0020] Step a, add 4-(1-adamantyl)aniline, o-bromochlorobenzene, Pd(dppf)Cl2, sodium tert-butoxide and toluene to the container, then heat to 85 degrees under stirring, react for 5 hours, stop heating , when the reaction is down to room temperature, sodium tert-butoxide and sodium bromide are removed by filtration, the organic phase is concentrated to about 50ml of solvent, a large amount of solid is precipitated, and then filtered to obtain N-(2 chlorophenyl)-4-(1-adamant Alkyl) aniline;

[0021] Step b, add N-(2-chlorophenyl)-4-(1-adamantyl)aniline obtained in step a into the container, add tert-butyl acetic acid, potassium carbonate and palladium acetate, and heat to 120 degrees under stirring , reacted for 5 hours, stopped heating, cooled to room temperature, filtered to remove potassium carbonate, and the filtered organic phase was concentrated to dryness, and recrystallize...

Embodiment 2

[0030] Under nitrogen protection, add 4-(1-adamantyl) aniline (100mmol, 22.7g), p-chlorobromobenzene (100mmol, 19.1g), sodium tert-butoxide (150mmol, 14.4g) into a dry container , [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (0.5mmol, 0.37g), 1,1'-binaphthyl-2,2'-bisdiphenylphosphine (2mmol , 1.25g), 300mL toluene, heated to 50 degrees, reacted for 32h, TLC monitored the completion of the reaction, cooled to room temperature, filtered off the inorganic salt, concentrated the organic phase to about 50ml solvent, precipitated a large amount of solid, filtered, and obtained intermediate M-1 27g, yield 80%.

[0031] Under nitrogen protection, add M-1 (85mmol, 28.5g), potassium carbonate (127.5mmol, 17.6g), palladium acetate (1.7mmol, 0.38g), tert-butyl acetic acid 200mL in a dry container, heat to 120 degree, reacted for 5h, TLC monitored the completion of the reaction, cooled to room temperature, filtered to remove inorganic salts, the organic phase was concentrate...

Embodiment 3

[0033] Under nitrogen protection, add 4-(1-adamantyl) aniline (100mmol, 22.7g), p-chlorobromobenzene (100mmol, 19.1g), sodium tert-butoxide (150mmol, 14.4g) into a dry container , [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (0.5mmol, 0.37g), 1,1'-binaphthyl-2,2'-bisdiphenylphosphine (2mmol , 1.25g), 300mL toluene, heated to 110 degrees, reacted for 32h, TLC monitored the completion of the reaction, cooled to room temperature, filtered off the inorganic salt, concentrated the organic phase to about 50ml of solvent, precipitated a large amount of solid, filtered, and obtained intermediate M-1 20.6g, yield 61%.

[0034] Under nitrogen protection, M-1 (85mmol, 28.5g), potassium carbonate (127.5mmol, 17.6g), palladium acetate (1.7mmol, 0.38g), 200mL of tert-butyl acetic acid were added to a dry 500mL three-necked flask, and heated To 120 degrees, react for 5h, TLC monitors the completion of the reaction, cool to room temperature, filter to remove inorganic salts, conc...

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Abstract

The invention discloses a preparation method of 3-(1-adamantyl) carbazole, which comprises the following steps: step a, adding 4-(1-adamantyl) aniline, o-bromochlorobenzene, Pd(dppf)Cl2, sodium tert-butoxide and methylbenzene into a container, heating while stirring, cooling to room temperature after the reaction is completed, filtering to remove sodium tert-butoxide and sodium bromide, concentrating to separate out a large amount of solid, and filtering to obtain N-(2-chlorophenyl)-4-(1-adamantyl) aniline; step b, adding the N-(2-chlorphenyl)-4-(1-adamantyl) aniline obtained in the step a into another container, adding tert-butyl acetic acid, potassium carbonate and palladium acetate, heating while stirring, reacting for 5 hours, cooling to room temperature after the reaction is completed, filtering to remove potassium carbonate, concentrating the substance after filtration, recrystallizing by using 3 times of ethyl acetate to obtain white solid that is 3-(1-adamantyl) carbazole. The 4-(1-adamantyl) aniline and o-bromochlorobenzene are used as initial raw materials, and the reaction operation process and post-treatment are simple.

Description

technical field [0001] The invention relates to the technical field of synthesis of organic materials and pharmaceutical intermediates, in particular to a preparation method of 3-(1-adamantyl)carbazole. Background technique [0002] The description of the background technology of the present invention and the relevant technologies related to the present invention are only used for illustration and to facilitate the understanding of the content of the present invention, and should not be understood as the applicant's definite or inferred that the applicant believes that the present invention is the application for the first application day's prior art. [0003] 3-(1-adamantyl)carbazole is an important intermediate widely used in the fields of polymers, optoelectronic materials and medicine. The use of organic electroluminescent (EL) components in solid-state light-emitting inexpensive large-area full-color display components has attracted much attention. Organic light-emitt...

Claims

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Application Information

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IPC IPC(8): C07D209/86
CPCC07D209/86
Inventor 姜珍华易炜陈俊利邵昌尧高然章明许传昊许延想
Owner 山东盛安贝新能源有限公司
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