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Method for synthesizing aromatic difluoroboron beta-diketonate compounds by one-pot process

A technology for diketone boron difluoride and aromatic compounds, which is applied in the field of one-pot synthesis of aryl-β-diketone boron difluoride compounds, can solve the problems of high cost and low yield, and achieve raw material cost Low, high yield and purity, simple operation

Active Publication Date: 2021-07-13
HIGH & NEW TECH RES CENT OF HENAN ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Literature Balaban, T.S.; Balaban, A.T.Product class 1:pyrylium salts.Scienceof Synthesis, 2003,14,11-200. A method for one-step synthesis of pyrylium salts is disclosed, which involves aryl-β-di Ketone boron difluoride complex, in this document, aryl ketone, acetic anhydride and boron trifluoride ether are mixed and heated to reflux, and the target product pyrylium salt, aryl-β-diketone, is obtained by a one-pot method Boron difluoride compounds appear as by-products with low yields
[0009] In addition, the current synthesis of aryl-β-diketone boron difluoride compounds is based on aryl ketones as raw materials, and aryl ketones are produced by acetylation of aromatic compounds, and the cost is relatively high
At present, there is no report on the one-pot synthesis of aryl-β-diketone boron difluoride compounds using aromatic compounds as raw materials

Method used

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  • Method for synthesizing aromatic difluoroboron beta-diketonate compounds by one-pot process
  • Method for synthesizing aromatic difluoroboron beta-diketonate compounds by one-pot process
  • Method for synthesizing aromatic difluoroboron beta-diketonate compounds by one-pot process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] In a three-necked flask equipped with a thermometer, add 1.08g of anisole, 5.2g of acetic anhydride, and 1.41g of boron trifluoride ether, stir magnetically and heat the oil bath to 100°C, keep it warm for 2h, then let it stand to cool to room temperature, add Dilute with ethyl acetate-petroleum ether mixed solvent (the volume ratio of ethyl acetate and petroleum ether is 2:1), filter out the insoluble solid, and concentrate the filtrate for recrystallization (recrystallization solvent is ethyl acetate-petroleum ether mixed solvent, acetic acid The volume ratio of ethyl ester and petroleum ether is 1:1) to separate out a yellow solid to obtain the target product [2,2-difluoro-6-(4-methoxyphenyl)-4-methoxybenzene substituted Base-2H-1,3,2-dioxaboron complex] with a yield of 82% and a purity of 97%.

[0058] For NMR characterization see figure 1 with figure 2 , the spectrogram data are as follows:

[0059] 1 HNMR:CDCl 3 , 2.37 (s, 3H); 3.92 (s, 3H); 6.47 (s, 1H); 6....

Embodiment 2

[0062] In a three-necked flask equipped with a thermometer, add 0.84 g of thiophene, 5.2 g of acetic anhydride, and 1.41 g of boron trifluoride ether, stir magnetically and heat in an oil bath to 100°C, keep it warm for 2 hours, then let it stand to cool to room temperature, and add ethyl acetate Ester-petroleum ether mixed solvent (the volume ratio of ethyl acetate and petroleum ether is 2:1) is diluted, and the insoluble solid is filtered out, and the filtrate is concentrated and purified by column chromatography (the solvent used for purification is ethyl acetate-petroleum ether mixed solvent , the volume ratio of ethyl acetate and petroleum ether is 1:1), to obtain the thiophene-substituted target product [2,2-difluoro-4-methyl-6-(thiophen-2-yl)-2H-1,3 , 2-Dioxyboron complex], yield 60%, purity 98%.

[0063] See attached picture for NMR characterization image 3 with Figure 4 , the spectrogram data are as follows:

[0064] 1 HNMR:CDCl 3 , 2.37 (s, 3H); 6.38 (s, 1H); ...

Embodiment 3

[0067] In a three-necked flask equipped with a thermometer, add 1.38g of m-xylylene dimethyl ether, 5.2g of acetic anhydride, and 1.41g of boron trifluoride ether, stir magnetically and heat to 100°C in an oil bath, keep it warm for 2h, then let it stand and cool to room temperature , adding ethyl acetate-petroleum ether mixed solvent (the volume ratio of ethyl acetate and petroleum ether is 2:1) to dilute, filter out the insoluble solid, and the filtrate is concentrated and purified by column chromatography (the solvent used for purification is ethyl acetate-petroleum ether Ether mixed solvent, the volume ratio of ethyl acetate and petroleum ether is 1:1), to obtain the target product [6-(2,4-dimethoxyphenyl)-2,2-dimethoxybenzene substituted Fluoro-4-methyl-2H-1,3,2-dioxaboron complex], yield 70%, purity 98%.

[0068] See attached picture for NMR characterization Figure 5 with Image 6 , the spectrogram data are as follows:

[0069] 1 HNMR:CDCl 3 ,2.33(s,3H);3.91(s,3H);...

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Abstract

The invention relates to the technical field of synthesis of fluorescent materials, and provides a method for synthesizing aromatic difluoroboron beta-diketonate compounds by a one-pot process. The aromatic difluoroboron beta-diketonate compounds are obtained by mixing active aromatic compounds, acetic anhydride and boron trifluoride diethyl etherate through the one-pot process and carrying out a three-component cascade reaction. The active aromatic compounds are adopted as raw materials for reaction, and the raw materials are low in cost and wide in source; the one-pot process is adopted, the active aromatic compounds, acetic anhydride and boron trifluoride diethyl etherate are directly mixed for cascade reaction, the operation is simple, no catalyst or harsh reaction conditions are needed, and the yield and purity of the product are high; furthermore, the reaction temperature is moderate, the reaction can be carried out under the condition of 100-120 DEG C, and the required time is short. When the aromatic difluoroboron beta-diketonate compounds are synthesized by adopting the method disclosed by the invention, the yield of the obtained product is 60-80%, and the purity is 98.5-99%.

Description

technical field [0001] The invention relates to the technical field of fluorescent material synthesis, in particular to a method for synthesizing aryl-β-diketone boron difluoride compounds in one pot. Background technique [0002] Aryl-β-diketone boron difluorides (BF 2 bdks) is a fluorescent dye with excellent properties. It has excellent properties in many aspects such as high fluorescence quantum yield, large molar absorptivity, high electron mobility, good stimulus responsiveness, and two-photon absorption. It is used in optoelectronic materials and nonlinear Optical materials and other fields have broad application prospects. [0003] At present, the reported synthesis methods of aryl-β-diketone boron difluoride compounds generally require at least two steps of reaction, and require more kinds of reagents, the synthesis route is long, and the post-treatment of the product is complicated. [0004] Literature Inagaki, Sho; Saito, Kai; Suto, Soichiro; Aihara, Hiromi; Sug...

Claims

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Application Information

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IPC IPC(8): C07F5/02
CPCC07F5/022
Inventor 张家祥李珂庆王华芬刘双燕付阳郭辉姜垒
Owner HIGH & NEW TECH RES CENT OF HENAN ACAD OF SCI
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