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Method for synthesizing 9-aryl fluorene compound

A technology for aromatic hydrocarbon compounds and compounds, which is applied in the field of synthesizing 9-arylfluorene compounds, can solve the problems of high price, high cost, and harsh reaction temperature conditions of 130°C, and achieve simple operation, small environmental impact, and less harsh reaction conditions Effect

Inactive Publication Date: 2015-07-22
WUHAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reaction substrate is relatively easy to obtain, and the process method is simple, but the required catalyst and auxiliary agent are palladium acetate and cesium carbonate, which are not only expensive but also highly polluting and poisonous, and the reaction temperature condition of 130°C is also relatively harsh.
The industrialization prospect of above-mentioned these synthesis processes is all bad

Method used

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  • Method for synthesizing 9-aryl fluorene compound
  • Method for synthesizing 9-aryl fluorene compound
  • Method for synthesizing 9-aryl fluorene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of 9-phenylfluorene:

[0031] Add 91mg of 2-phenylbenzaldehyde (0.5mmol), 5ml of benzene and 4.4μL of trifluoromethanesulfonic acid (0.05mmol) to the test tube successively, stir for one minute, add 95μL of acetic anhydride (1mmol), and react at room temperature for 24h to obtain Reaction mixture (reaction time is determined according to thin-layer chromatographic analysis, stop when the reaction of raw materials is complete), the obtained reaction mixture is used to remove the solvent by vacuum distillation, and column chromatography (eluent is pure petroleum ether) is used to react crude oil. The product is purified to obtain the product. The yield was 28%.

[0032] Adopt nuclear magnetic resonance (NMR) method to test the product prepared in this embodiment, such as figure 1 and figure 2 , are respectively the product obtained in this example 1 H NMR spectrum and 13 C NMR spectrum, where 1 H NMR (400MHz, CDCl 3 ) data are: δ7.90(2H,d,J7.6),7.48(2H,t...

Embodiment 2

[0037] Synthesis of 2-tert-butyl-9-(2,4,6-trimethylphenyl)fluorene:

[0038] Add 5 mL of 1,2-dichloroethane, 119 mg of 2-(4-tert-butylphenyl)benzaldehyde (0.5 mmol), 348 μL of 1,3,5-trimethylbenzene (2.5 mmol) and 4.4 μL of trifluoroform to the test tube in sequence Sulfuric acid (0.05mmol), after stirring for one minute, add 95μL acetic anhydride (1mmol), and react at room temperature for 17h (the reaction time is determined by thin-layer chromatography analysis, stop when the reaction of raw materials is complete). The resulting reaction mixture was distilled under reduced pressure to remove the solvent, and the crude reaction product was purified by column chromatography (the eluent was pure petroleum ether) to obtain the product. The product yield is greater than 99%.

[0039] Adopt nuclear magnetic resonance (NMR) method to test the product prepared in this embodiment, such as image 3 and Figure 4 , are respectively the product obtained in this example 1 H NMR spect...

Embodiment 3

[0042] Synthesis of 9-(9-anthracenyl)fluorene:

[0043] Add 5mL of 1,2-dichloroethane, 91mg (0.5mmol) of 2-phenylbenzaldehyde, 96mg (0.54mmol) of anthracene and 4.4μL of trifluoromethanesulfonic acid (0.05mmol) to the test tube, and stir for one minute Add 95 μL of acetic anhydride (1 mmol), react at room temperature for 4 hours (the reaction time is determined by thin-layer chromatography analysis, stop when the reaction of the raw materials is complete), the obtained reaction mixture is removed by vacuum distillation, and column chromatography (elution The liquid is pure petroleum ether) to purify the reaction crude product to obtain the product. The product yield was 88%.

[0044] Adopt nuclear magnetic resonance (NMR) method to test the product prepared in this embodiment, such as Figure 5 and Image 6 , are respectively the product obtained in this example 1 H NMR spectrum and 13 C NMR spectrum, where 1 H NMR (400MHz, CDCl 3 ) data are: δ8.48(1H,d,J8.9),8.28(1H,s)...

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Abstract

The invention relates to a method for synthesizing a 9-aryl fluorene compound. The method is characterized in that 2-aryl benzaldehyde and an aromatic hydrocarbon compound are taken as the raw materials, trifluoromethane sulfonic acid and acetic anhydride are taken as the catalysts, and the cascade reaction of all the materials is carried out in an organic solvent at the room temperature for 1-30h to obtain the product; and then the product is purified to obtain the 9-aryl fluorene compound. The synthetic method is simple and convenient in steps, mild in conditions, and high in yield; the yield can be 28-99%.

Description

technical field [0001] The invention belongs to the technical field of synthesis of organic intermediates, in particular to a method for synthesizing 9-aryl fluorene compounds. Background technique [0002] Studies in recent years have proved that the polymers of fluorene and its derivatives are an important class of organic polymers with extremely photo- and electrical activity. , Red, blue and green primary color luminescent materials with high luminous efficiency. 9-arylfluorene compounds are important intermediate materials used to synthesize these luminescent materials, which have the structural formula (I). [0003] [0004] At present, the method of synthesizing 9-aryl fluorene compounds is mainly through the following routes: ① Li et al. used 2-aryl benzaldehyde as raw material to prepare diaryl carbinol and its esterified derivatives through Grignard (Grignard) reaction , and then perform intramolecular Friedel-Craft reaction with aromatic hydrocarbons under th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C13/54C07C13/573C07C1/20C07C25/22C07C22/08C07C17/363C07C43/21C07C41/18C07C211/54C07C209/68C09K11/06
Inventor 张方林李青翠徐文刚胡佳兴陈小清张津甫郑化
Owner WUHAN UNIV OF TECH
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