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Method for synthesizing fluorofluorenone compound

A technology of fluorinated fluorenones and compounds, which is applied in the field of preparation of fluorinated fluorenones, can solve the problems of expensive transition metal catalysts, toxicity, etc., and achieve the effects of good substrate adaptability, simple reaction steps, and mild reaction conditions

Active Publication Date: 2015-09-09
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method generally requires the use of expensive transition metal catalysts or toxic ligands

Method used

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  • Method for synthesizing fluorofluorenone compound
  • Method for synthesizing fluorofluorenone compound
  • Method for synthesizing fluorofluorenone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]

[0037] Mix 0.3mmol (E)-1-(2'-tert-butylethynyl)-3-p-tolyl-2-allyl ketone (90.6mg), 0.6mmol Selectfluor (212.4mg) and 0.015mmol Cu powder (0.96mg ) was added to a 15mL thick-walled pressure-resistant reaction tube, and then 3mL of acetonitrile was added as a solvent. Next, magnetic stirring was performed at 50° C. for 1.5 hours. After cooling to room temperature, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and then separated by column chromatography, using petroleum ether / dichloromethane=5:1 as eluent, collect the eluent containing the product, evaporate the solvent from the eluent to obtain 7-methyl-5-fluoro-11H-benzofluorenone. The material was a yellow solid in 70% yield.

[0038] Characterization data: IR(KBr,cm -1 ):ν=1705 (C=O); 1 H NMR (500MHz, CDCl 3 ): δ7.97(s,1H),7.91(d,J=7.5Hz,1H),7.88(s,1H),7.81(d,J=8.0Hz,1H),7.77(d,J=7.5Hz ...

Embodiment 2

[0040]

[0041]0.3 mmol (E)-1-(2'-tert-butylethynyl)-3-p-tolyl-2-allylone (90.6 mg), 0.4 mmol Selectfluor (141.7 mg) and 0.015 mmol Cu (0.96 mg) Add the powder into a 15mL thick-walled pressure-resistant reaction tube, and then add 3mL DMF as a solvent. Next, magnetic stirring was performed at 60° C. for 1.5 hours. After cooling to room temperature, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and then separated by column chromatography, using petroleum ether / dichloromethane=5:1 as eluent, collect the eluate containing the product, evaporate the solvent from the eluate to obtain 7-methyl-5-fluoro-11H-benzofluorenone. The material was a yellow solid, 60% yield.

[0042] Characterization data: IR(KBr,cm -1 ):ν=1705 (C=O); 1 H NMR (500MHz, CDCl 3 ): δ7.97(s,1H),7.91(d,J=7.5Hz,1H),7.88(s,1H),7.81(d,J=8.0Hz,1H),7.77(d,J=7.5Hz ,1H),7.60(t,J=7.5Hz,1H),...

Embodiment 3

[0044]

[0045] 0.3mmol (E)-1-(2'-tert-butylethynyl)-3-p-tolyl-2-allyl ketone (90.6mg), 0.6mmol N-fluoropyridine trifluoromethanesulfonate (147.6mg) and 0.015 mmol CuCN (1.35 mg) powder were added to a 15 mL thick-walled pressure-resistant reaction tube, and then 3 mL of acetonitrile was added as a solvent. Next, magnetic stirring was performed at 45° C. for 2.5 hours. After cooling to room temperature, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and then separated by column chromatography, using petroleum ether / dichloromethane=5:1 as eluent, collect the eluate containing the product, evaporate the solvent from the eluate to obtain 7-methyl-5-fluoro-11H-benzofluorenone. The material was a yellow solid, 68% yield.

[0046] Characterization data: IR(KBr,cm -1 ):ν=1705 (C=O); 1 H NMR (500MHz, CDCl 3 ): δ7.97(s,1H),7.91(d,J=7.5Hz,1H),7.88(s,1H),7.81...

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Abstract

The invention discloses a method for synthesizing a fluorofluorenone compound. the method is characterized in that a o-t-butyl ethynyl chalcone compound as shown in the formula 1 is used as a raw material to react in an organic solvent under the action of a copper catalyst and a fluorine oxidizer at the temperature of 25-60 DEG C for 0.5-6 h; and a reaction liquid undergoes separation and purification to prepare the fluorofluorenone compound as shown in the formula 2. The method has advantages of simple reaction steps, good substrate universality, mild reaction condition, safety and environmental protection, etc. According to the method, various fluoride-free nonaromatic chalcones are directly used as raw materials and cheap copper is used as a catalyst. The method is a new route for synthesizing various fluorofluorenone compounds containing a substituent group.

Description

technical field [0001] The invention relates to a preparation method of fluorofluorenone compounds. Background technique [0002] Fluorenone is the raw material of important fine chemicals, and has a wide range of applications in dyes, medicines and pesticides. In addition, fluorenone is also used in polymer materials (such as fluorene resin) and photoconductive materials (such as 2,4,7-trinitrofluorenone). There are two main methods for the synthesis of traditional fluorenones: one is the synthesis method using non-fluorene as the raw material, which generally uses alkyl carboxylic acid or alkyl ester as the raw material, and is synthesized by aromatization at high temperature (>250°C). Fluorenone; the other is the oxidation reaction of fluorene, the reaction conditions of this method are generally harsh and easy to produce organic or inorganic waste. In recent decades, based on the continuous deepening of transition metal-catalyzed C-H bond functionalization reactions...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/697C07C49/755C07C45/63
CPCC07C45/63C07C49/697C07C49/755
Inventor 刘运奎张剑张巍
Owner ZHEJIANG UNIV OF TECH
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