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

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

Inactive Publication Date: 2017-04-12
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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  • Synthetic method of 2-bromo-9,9-diphenylfluorene
  • Synthetic 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 comprises the following steps:

[0026] (1) Mix 10 mmol 2-bromo-9-phenyl-fluoren-9-ol and 100 mmol benzene, heat up to 61°C under stirring, and feed hydrogen chloride gas until the raw material point (2-bromo-9- Phenyl-fluorene-9-ol) basically disappeared. After ventilation, the reaction system was heated up to the reflux temperature, and refluxed for 1 hour. While refluxing, use a water separator to separate the water in the system;

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

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

Embodiment 2

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

[0031] (1) Mix 10 mmol 2-bromo-9-phenyl-fluoren-9-ol and 180 mmol benzene, heat up to 66°C under stirring, and pass in hydrogen iodide gas until the raw material point basically disappears as monitored by TLC, and the ventilation is completed Finally, the reaction system was warmed up to the reflux temperature, and the reflux was completed for 1.5 h, and the moisture in the system was separated by a water separator while refluxing;

[0032] (2) Cool the system to 18±2°C, add the catalyst in batches within 0.5h, complete the addition, raise the temperature to 50°C for 4.5h and end; the catalyst consists of 12mmol anhydrous aluminum trichloride and 3mmol anhydrous trichloride Composed of iron oxide, the catalyst was added in three batches, and the weight ratio of the three additions was 3:2:1;

[0033] (3) Separation and purification to obtain 2-bromo-9,9-diphenylfluorene. The separatio...

Embodiment 3

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

[0036] (1) Mix 10 mmol of 2-bromo-9-phenyl-fluoren-9-ol and 170 mmol of benzene, heat up to 64°C under stirring, and inject sufficient amount of hydrogen bromide gas until the raw material point basically disappears as monitored by TLC. After the ventilation is completed, the reaction system is heated to the reflux temperature, and the reflux is completed for 2 h, and the water in the system is separated by a water separator while reflux;

[0037] (2) Cool the system to 20±2°C, add the catalyst in batches within 1h, after the addition is completed, heat up to 45°C and react for 5h; the catalyst consists of 12mmol anhydrous aluminum trichloride and 3mmol anhydrous ferric chloride Composition, the catalyst is added in three batches, and the weight ratio of the three additions is 3:2:1;

[0038] (3) Separation and purification to obtain 2-bromo-9,9-diphenylfluorene. The separation and pu...

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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, Shun Li et al. (Journal of Organic Chemistry, 75 (12), 4004-4013, 2010) proposed using trifluoromethanesulfonic acid as a d...

Claims

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Application Information

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Patent Type & Authority Patents(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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