Synthesis method of 2-bromo-9,9-diphenylfluorene

A technology of diphenylfluorene and synthesis method, which is applied in the fields of chemical instruments and methods, preparation of halogenated hydrocarbons, organic chemistry, etc., can solve the problems of expensive trifluoromethanesulfonic acid, difficult post-processing, high cost, etc., and achieve good catalytic effect , product yield improvement, simple operation effect

Inactive Publication Date: 2015-11-25
河南普利泰新材料研究院有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are problems such as low yield in this method, difficulty in post-processing and high cost of trifluoromethanesulfonic acid

Method used

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  • Synthesis method of 2-bromo-9,9-diphenylfluorene
  • Synthesis method of 2-bromo-9,9-diphenylfluorene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The synthetic method of 2-bromo-9,9-diphenylfluorene includes the following steps:

[0026] (1) Mix 10mmol 2-bromo-9-phenyl-fluorene-9-alcohol with 100mmol benzene, heat up to 61℃ with stirring, and pass in hydrogen chloride gas until TLC monitors the raw material point (2-bromo-9-phenyl -Fluorene-9-alcohol) has basically disappeared. After the aeration is completed, the reaction system is heated to the reflux temperature, refluxed for 1 hour, and the water in the system is separated by a water separator while refluxing;

[0027] (2) Cool the system to 17±2°C, add the catalyst in batches within 0.5h, after the addition, heat up to 35°C and react for 3.5h; the catalyst consists of 10mmol anhydrous aluminum trichloride and 1mmol anhydrous trichloride It is composed of iron, the catalyst is added in three batches, and the weight ratio of the three additions is 3:2:1;

[0028] (3) Separate and purify to obtain 2-bromo-9,9-diphenylfluorene. The separation and purification operatio...

Embodiment 2

[0030] The synthetic method of 2-bromo-9,9-diphenylfluorene includes the following steps:

[0031] (1) Mix 10mmol of 2-bromo-9-phenyl-fluorene-9-ol and 180mmol of benzene. The temperature is raised to 66°C with stirring, and hydrogen iodide gas is introduced until the raw material point disappears after TLC monitoring. After the ventilation is completed, The reaction system is heated to the reflux temperature, and the reflux is completed for 1.5 hours, and the water in the system is separated by a water separator while refluxing;

[0032] (2) Cool the system to 18±2℃, add the catalyst in batches within 0.5h. After the addition is completed, the temperature is raised to 50℃ and the reaction ends after 4.5h; the catalyst consists of 12mmol anhydrous aluminum trichloride and 3mmol anhydrous trichloride It is composed of iron, the catalyst is added in three batches, and the weight ratio of the three additions is 3:2:1;

[0033] (3) Separate and purify to obtain 2-bromo-9,9-diphenylfluor...

Embodiment 3

[0035] The synthetic method of 2-bromo-9,9-diphenylfluorene includes the following steps:

[0036] (1) Mix 10mmol 2-bromo-9-phenyl-fluorene-9-alcohol and 170mmol benzene, heat up to 64℃ with stirring, and pass in enough hydrogen bromide gas until TLC monitors that the raw material point has almost disappeared and the ventilation is complete Afterwards, the reaction system was heated to the reflux temperature, and the reflux was completed for 2 hours, and the water in the system was separated by a water separator while refluxing;

[0037] (2) Cool the system to 20±2℃, add the catalyst in batches within 1h. After the addition is completed, the temperature is raised to 45℃ and the reaction is finished after 5h; the catalyst consists of 12mmol anhydrous aluminum trichloride and 3mmol anhydrous iron trichloride Composition, the catalyst is added in three batches, and the weight ratio of the three additions is 3:2:1;

[0038] (3) Separate and purify to obtain 2-bromo-9,9-diphenylfluorene....

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Abstract

The invention provides a synthesis method of 2-bromo-9,9-diphenylfluorene and belongs to the technical field of organic synthesis. The synthesis method comprises steps as follows: (1), after 2-bromo-9-phenyl-fluorene-9-ol and benzene are mixed, reaction gas is introduced for a reaction at the temperature of 61-66 DEG C while the components are stirred, the temperature is increased and backflow is performed after gas introduction is finished, and water is separated while backflow is performed; (2), a catalyst is added in 0.5-1 h after a system obtained from the step (1) is cooled, the temperature is increased to 35-50 DEG C, and the mixture reacts for 3.5-5 h; (3), 2-bromo-9,9-diphenylfluorene is obtained through separation and purification. The synthesis method of 2-bromo-9,9-diphenylfluorene is low in cost, especially when hydrogen chloride and hydrogen bromide are utilized; with the adoption of an aluminum trichloride anhydrous and ferric chloride anhydrous mixed catalysis mode, the catalysis effect is good, the reaction time is short, and the yield is high; the operation is simple, the process is reliable, and scale-up is facilitated.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a synthesis method of 2-bromo-9,9-diphenylfluorene. Background technique [0002] As a new type of organic semiconductor material, organic electroluminescent materials have potential commercial application value in light-emitting diodes, solar cells and other fields due to their high luminous efficiency and simple device manufacturing process. Among them, fluorene compounds are an ideal Material. Fluorene and its derivatives have the characteristics of large conjugated system in the molecule, rigid planar biphenyl structure, wide energy gap, high luminous efficiency, and easy structure modification, so they are used in electroluminescent materials, Solar cell materials and other fields have a wide range of applications. [0003] Chang, ShunLi et al. (JournalofOrganicChemistry, 75(12), 4004-4013, 2010) proposed to use trifluoromethanesulfonic acid as dehydra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C25/22C07C17/266
Inventor 王永王法云张立攀郭青照罗蓓蓓任钊张亚勋李栋
Owner 河南普利泰新材料研究院有限公司
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