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3-bromofluorenone preparation method

A technology of bromofluorenone and fluorenone, which is applied in the field of preparation of 3-bromofluorenone, can solve the problems of difficult to meet organic optoelectronic materials, difficulty in product purification, long reaction route, etc., and achieve broad market prospects, low cost, and preparation The effect of simple method

Active Publication Date: 2017-08-18
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this route is that the reaction route is too long, and involves diazotization reaction, the safety is poor, the purification of the obtained product is difficult, and it is difficult to meet the requirements of organic photoelectric materials.

Method used

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  • 3-bromofluorenone preparation method

Examples

Experimental program
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Effect test

Embodiment 1

[0033] Preparation of fluorenone methoxyxime: Dissolve 36.0g (200mmol) fluorenone, 17.5g (210mmol) methoxyamine hydrochloride and 13g (122mmol) sodium carbonate in 250mL methanol solution, heat up to 60-65°C, and stir for reaction 3.0hrs. Cool down to room temperature, add 100g and 200g chloroform to the reaction system, separate layers, wash the organic phase with 100mL of water, dry over anhydrous sodium sulfate, and remove the solvent in vacuo to obtain 41.6g of crude fluorenone methoxyxime, with a yield of 99.52%, without purification, directly for the next step.

[0034] Preparation of 3-bromofluorenone methoxyxime: 21.0g (100mmol) fluorenone methoxyxime and 1g (7.5mmol) aluminum trichloride were added to 200g dichloroethane, fully replaced by nitrogen, at 50 C bromine dichloroethane mixture (15.9g (100mmol) bromine + 100g dichloroethane) was added dropwise. The dropwise addition took about 1 hour. After the reaction was completed, 100mL of saturated aqueous sodium bisu...

Embodiment 2

[0043] Preparation of fluorenone methoxyxime: Dissolve 36.0g (200mmol) fluorenone, 16.7g (200mmol) methoxyamine hydrochloride and 11.7g (110mmol) sodium carbonate in 250mL methanol solution, heat up to 60-65°C, stir Response 3.0hrs. Cool down to room temperature, add 100g and 200g chloroform to the reaction system, separate layers, wash the organic phase with 100mL of water, dry over anhydrous sodium sulfate, and remove the solvent in vacuo to obtain 41.4g of crude fluorenone methoxyxime, with a yield of 99.04%, without purification, directly for the next step.

[0044] Preparation of 3-bromofluorenone methoxyxime: 21.0g (100mmol) fluorenone methoxyxime and 0.7g (5mmol) aluminum trichloride were added to 200g dichloroethane, fully replaced by nitrogen, at 60 C bromine dichloroethane mixture (14.3g (90mmol) bromine + 100g dichloroethane) was added dropwise. The dropwise addition took about 1 hour. After the reaction was completed, 100mL of saturated aqueous sodium bisulfite s...

Embodiment 3

[0053] Preparation of fluorenone methoxyxime: Dissolve 36.0g (200mmol) fluorenone, 18.4g (220mmol) methoxyamine hydrochloride and 13g (122mmol) sodium carbonate in 250mL ethanol solution, heat up to 70-75°C, and stir for reaction 3.0hrs. Cool down to room temperature, add 100g and 200g chloroform to the reaction system, separate layers, wash the organic phase with 100mL of water, dry over anhydrous sodium sulfate, and remove the solvent in vacuo to obtain 41.8g of crude fluorenone methoxyxime, with a yield of 100%, without purification, directly for the next step.

[0054] Preparation of 3-bromofluorenone methoxyxime: 21.0g (100mmol) fluorenone methoxyxime and 1.3g (10mmol) aluminum trichloride were added to 200g dichloroethane, fully replaced by nitrogen, at 40 C bromine dichloroethane mixture (15.2g (95mmol) bromine + 100g dichloroethane) was added dropwise. The dropwise addition took about 1 hour. After the reaction was completed, 100mL of saturated aqueous sodium bisulfi...

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Abstract

The invention belongs to the technical field of fluorine compound preparation, in particular to a 3-bromofluorenone preparation method. The 3-bromofluorenone preparation method comprises the following steps: A, oximation reaction: adding fluorenone and methoxamine hydrochloride into a solvent, performing oximation reaction, and performing reaction quenching to obtain fluorenone methoxy oxime; B, bromination reaction: adding a catalyst, bromine and the fluorenone methoxy oxime obtained in the step A into the solvent, and performing reaction quenching to obtain a bromide product; C, hydrolysis reaction: adding the bromide product obtained in the step B into the solvent, and performing hydrolysis reaction at the temperature of 50 to 100 DEG C to obtain 3-bromofluorenone. The preparation method is simple and low in cost, the obtained 3-bromofluorenone is high in yield and high in purity, the reaction conditions are mild, and the 3-bromofluorenone is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of preparation of fluorene compounds, and in particular relates to a preparation method of 3-bromofluorenone. Background technique [0002] As a class of electroluminescent materials with a rigid planar biphenyl structure, fluorene compounds have attracted much attention due to their wide energy gap and high luminous efficiency. Fluorenone derivatives are used as electron transport materials in organic photoconductor (OLED) devices. been widely used in. The introduction of halogenated fluorenone compounds into molecules with electroluminescent properties is of great significance for improving the thermal stability and spectral stability of molecules; the substituted aryl Schiff base compounds of halogenated fluorenones have photochromic properties; and Halogenated fluorenones are important multifunctional intermediates. The most representative of such compounds is 3-bromofluorenone. [0003] There are man...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/42C07C49/697
CPCC07C45/42C07C249/04C07C249/12C07C49/697C07C251/44
Inventor 慈振华林存生马永洁石宇胡葆华孟凡民
Owner VALIANT CO LTD
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