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A kind of method for preparing high-purity 4-bromofluorene

A high-purity, bromofluorene technology, applied in the preparation of halogenated hydrocarbons, chemical instruments and methods, organic chemistry, etc., can solve the problems affecting the performance of finished materials OLED devices, etc., and achieve the effect of high purity

Active Publication Date: 2016-04-06
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] With the development of OLED optoelectronic materials, the requirements for the purity of raw materials are gradually increasing. At present, the content of dibromofluorene in the product obtained by the conventional synthesis method of 4-bromofluorene is relatively high, which seriously affects the performance of the OLED device of the finished material. Therefore, high-purity 4-bromofluorene is prepared. -Bromofluorene has gradually attracted the attention of scientific and technological workers

Method used

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  • A kind of method for preparing high-purity 4-bromofluorene
  • A kind of method for preparing high-purity 4-bromofluorene
  • A kind of method for preparing high-purity 4-bromofluorene

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Embodiment 1

[0026] Preparation of 2,7-di-tert-butylfluorene: Dissolve 6.0g (36.0mmol) fluorene in 25ml dichloroethane solution, add 10g (75mmol) aluminum trichloride, control the internal temperature at 10-15°C, add dropwise Chloro-tert-butane 7.0g (76mmol), it took 15min to add dropwise, the reaction mixture was reacted at 10-15°C for 30min, the reaction system was slowly poured into 100g of crushed ice, the layers were separated, the aqueous phase was extracted with 50ml of dichloroethane, combined The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed in vacuo to obtain 9.6 g of crude 2,7-di-tert-butylfluorene, with a yield greater than 100% and a GC purity of 99.29%;

[0027] Preparation of 2,7-di-tert-butyl-4-bromofluorene: Dissolve 9g (34mmol) 2,7-di-tert-butylfluorene in 40ml methanol solution, heat to 25°C, add dropwise 12.6g (32mmol) benzyl Trimethylammonium tribromide and 200ml of dichloromethane solution mixed solution, 2.0hrs added, heat preserv...

Embodiment 2

[0032] Preparation of 2,7-di-tert-butylfluorene: Dissolve 6.0g (36.0mmol) fluorene in 25ml dichloroethane solution, add 11.5g (86mmol) aluminum trichloride, control internal temperature 0-5°C, drop Add 7.0 g (76 mmol) of tert-butyl chloride, dropwise for 15 min, react the reaction mixture at 0-5°C for 60 min, slowly pour the reaction system into 100 g of crushed ice, separate layers, extract the aqueous phase with 50 ml of dichloroethane, The organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was removed in vacuo to obtain 9.5 g of crude 2,7-di-tert-butylfluorene, with a yield of 100% and a GC purity of 99.4%;

[0033] Preparation of 2,7-di-tert-butyl-4-bromofluorene: Dissolve 9g (34mmol) 2,7-di-tert-butylfluorene in 40ml methanol solution, heat to 30°C, add dropwise 13.2g (34mmol) benzyl The mixture of ethyl ethyl ammonium tribromide and 80ml dichloromethane solution, after 1.0hrs addition, keep warm for 1.0hrs, add water to quench the reaction...

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Abstract

The invention relates to a novel method for preparing high-purity 4-bromofluorene. The novel method comprises the following steps: by taking dichloroethane as a solvent and aluminum trichloride as a catalyst, enabling fluorene and 2-chloro-2-methylpropane to be in Friedel-Crafts reaction to obtain a 2,7-di-tert-butyl fluorene crude product; carrying out bromination on the 2,7-di-tert-butyl fluorene crude product by virtue of a high-selectivity bromination reagent to obtain 2,7-di-tert-butyl-4-bromofluorene; removing tertiary butyl from the 2,7-di-tert-butyl-4-bromofluorene by virtue of lewis acid to obtain 4-bromofluorene; re-crystallizing with alcohol at a reaction temperature of 10 DEG C-50 DEG C to obtain 4-bromofluorene. The 4-bromofluorene prepared by the method is high in purity and has GC purity of 99.9%, dibromofluorene content less than 100ppm and good application prospect.

Description

technical field [0001] The invention relates to a new method for preparing high-purity 4-bromofluorene, which belongs to the field of organic synthesis. Background technique [0002] In recent years, with the development and application of organic optoelectronic materials, the research on fluorene compounds has received widespread attention. First, the structure of fluorene has high light and thermal stability, and its fluorescence quantum efficiency in solid state is as high as 60%-80%, and its energy gap is greater than 2.90eV. As one of the fluorene derivatives, 4-bromofluorene is widely used in the field of optoelectronic materials, especially in the field of OLED light-emitting materials, so the research on its synthesis method is of great significance. [0003] At present, the preparation methods of 4-bromofluorene reported in literature at home and abroad are mainly the following two kinds: [0004] 1. In the document J.A.C.S, 2014, 136(2), P801~809, 2,2-dibromobiph...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C17/361C07C25/22
Inventor 林存生付文岗高宪鹏孙虎代树华巩玉喜
Owner VALIANT CO LTD