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Preparation method of 3-halogenated fluorenone compound

A technology of halogenated fluorenones and compounds, which is applied in the field of preparation of 3-halogenated fluorenones, can solve the problems of 3-bromofluorenones being expensive and difficult to prepare, and achieve short cycle times, simple operations, and mild reaction conditions Effect

Inactive Publication Date: 2016-02-03
烟台九目化学股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is that 3-bromofluorene is expensive and difficult to prepare

Method used

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  • Preparation method of 3-halogenated fluorenone compound
  • Preparation method of 3-halogenated fluorenone compound
  • Preparation method of 3-halogenated fluorenone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] 1) Preparation of Compound A

[0037]

[0038] Under nitrogen protection, 2-bromo-4-nitrobenzoic acid methyl ester (6.5g, 0.025mol), phenylboronic acid (3.2g, 0.0262mol) and 30% mass fraction of potassium carbonate aqueous solution ( Potassium carbonate: 8.637g, 0.0625mol; water: 20.16g), in solvent toluene (19.5g), catalyst palladium acetate (0.0056g, 7.5*10 -5 mol) and ligand triphenylphosphine (0.0393g, 1.5*10 -4 mol) in the presence of the mixture, the temperature was raised to 55-60° C., and the reaction was complete for 2 hours (TLC followed the reaction). After the reaction, the mixture was cooled to 0-40°C, the aqueous phase was separated by liquid separation, the organic phase was washed with water to pH = 7, dried over anhydrous sodium sulfate, passed through a silica gel column, and concentrated by rotary evaporation to obtain a brownish yellow solid, which was weighed with toluene Crystallized to obtain a pale yellow solid, dried in vacuo to obtain 5.7 ...

Embodiment 2

[0054] 1) Preparation of Compound A

[0055]

[0056] Under nitrogen protection, 2-bromo-4-nitrobenzoic acid methyl ester (6.5g, 0.025mol), phenylboronic acid (3.2g, 0.0262mol) and 30% mass fraction of potassium carbonate aqueous solution ( Potassium carbonate: 8.637g, 0.0625mol; water: 20.16g), in solvent toluene (19.5g), catalyst palladium acetate (0.0056g, 7.5*10 -5 mol) and ligand tricyclohexylphosphine (0.042g, 1.5*10 -4 mol) in the presence of the mixture, the temperature was raised to 55-60° C., and the reaction was complete for 2 hours (TLC followed the reaction). After the reaction, the mixture was cooled to 0-40°C, the aqueous phase was separated by liquid separation, the organic phase was washed with water to pH = 7, dried over anhydrous sodium sulfate, passed through a silica gel column, and concentrated by rotary evaporation to obtain a brownish yellow solid, which was weighed with toluene Crystallized to obtain a pale yellow solid, dried in vacuo to obtain 5...

Embodiment 3

[0072] 1) Preparation of Compound A

[0073]

[0074] Under nitrogen protection, 2-bromo-4-nitrobenzoic acid methyl ester (6.5g, 0.025mol), phenylboronic acid (3.2g, 0.0262mol) and 30% mass fraction of potassium carbonate aqueous solution ( Potassium carbonate: 8.637g, 0.0625mol; water: 20.16g), in solvent toluene (19.5g), catalyst palladium acetate (0.0056g, 7.5*10 -5 mol) and ligand tricyclohexylphosphine (0.042g, 1.5*10 -4 mol) in the presence of the mixture, the temperature was raised to 55-60° C., and the reaction was complete for 2 hours (TLC followed the reaction). After the reaction, the temperature of the mixture was lowered to 0-40°C, the aqueous phase was separated through liquid separation, the organic phase was washed with water to pH = 7, dried over anhydrous sodium sulfate, passed through a silica gel column, and concentrated by rotary evaporation to obtain a brownish-yellow solid, which was weighed with toluene Crystallized to obtain a pale yellow solid, d...

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Abstract

The invention relates to a preparation method of a 3-halogenated fluorenone compound. According to the method, 2-bromine-4-nitrobenzoic acid methyl ester is used as a starting material, and through Suzuki reaction, reduction reaction, diazotization reaction and ring closing reaction, the 3-halogenated fluorenone compound is prepared. When the method is adopted for synthesizing the 3-halogenated fluorenone, the cost is low; the condition is mild; the operation is simple; the preparation method is suitable for laboratories and industrial large-scale preparation.

Description

technical field [0001] The invention relates to a preparation method of 3-halogenated fluorenone compounds, belonging to the field of chemistry. 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] The preparation method of 3-bromofluorenone di...

Claims

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Application Information

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IPC IPC(8): C07C45/45C07C49/697
CPCC07C45/455C07C67/307C07C201/12C07C227/06C07C49/697C07C69/65C07C229/60C07C205/57
Inventor 陈慕欣宋贺柳佳欣胡晓腾储毅孙海洋
Owner 烟台九目化学股份有限公司
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