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Method for preparing benzfluorenone compound by palladium as catalyst

The technology of benzofluorenone and palladium catalyst is applied in the synthesis field of organic compounds, can solve the problems of difficult preparation of reaction raw materials, numerous reaction steps, long reaction time and the like, and achieves high substrate universality, easy preparation and simple operation. Effect

Active Publication Date: 2015-11-25
HUAWEI TEHCHNOLOGIES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to solve the problems that the reaction raw materials are not easy to prepare, the reaction temperature is high, the reaction steps are various, the yield is low, and the reaction time is long in the synthesis method of benzofluorenone and its derivatives at present, the present invention proposes a method using palladium as The preparation method of catalyst benzofluorenone compounds, the present invention uses base metals instead of expensive noble metals to realize the reaction under milder conditions

Method used

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  • Method for preparing benzfluorenone compound by palladium as catalyst
  • Method for preparing benzfluorenone compound by palladium as catalyst
  • Method for preparing benzfluorenone compound by palladium as catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Synthesis of 5-phenylbenzofluorenone using 3-phenyl-1-(2'-o-methylphenylethynyl)phenyl-2-allyl ketone as raw material

[0027]

[0028] Add 0.2mmol of 3-phenyl-1-(2'-o-methylphenylethynyl)phenyl-2-allyl ketone, 0.01mmol of Pd / C and 0.4mmol of Selectfluor into a 10mL pressure-resistant sealed container in sequence, and then add 2.0 mL of acetonitrile. Stir the reaction at room temperature, TLC follow-up detection, after 3 hours of reaction, the reaction solution is diluted with 10mL of dichloromethane, filtered to obtain the clear liquid, and the solvent is removed by column chromatography (eluent ratio: sherwood oil to acetic acid Ethyl ester (volume ratio 15:1) was separated, the eluate was collected, and the solvent was distilled off to obtain 5-o-methylphenylbenzofluorenone as an orange solid with a yield of 75%.

[0029] Orange solid; mp213-215℃; 1 HNMR (500MHz, CDCl 3 ): δ=8.26(s, 1H), 8.00-7.96(m, 1H), 7.76(dd, J 1 =6.0Hz,J 2 =1.0Hz, 1H), 7.52-7...

Embodiment 2

[0030] Example 2: Synthesis of 5-phenylbenzofluorenone using 3-phenyl-1-(2'-o-methylphenylethynyl)phenyl-2-allyl ketone as raw material

[0031]

[0032] 0.2mmol of 3-phenyl-1-(2'-o-methylphenylethynyl)phenyl-2-allyl ketone, 0.02mmol of Pd / C and 1-chloromethyl-4-fluoro-1,4-di Add 0.6mmol of azabicyclo[2.2.2]octane di(hexafluorophosphate) salt into a 10mL pressure-resistant sealed container in turn, and then add 2.0mL of chloroform. Stir the reaction at room temperature, TLC follow-up detection, after 3 hours of reaction, the reaction solution is diluted with 10mL of dichloromethane, filtered to obtain the clear liquid, and the solvent is removed by column chromatography (eluent ratio: sherwood oil to acetic acid Ethyl ester (volume ratio 15:1) was separated, the eluate was collected, and the solvent was distilled off to obtain 5-o-methylphenylbenzofluorenone as an orange solid with a yield of 70%.

[0033] Orange solid; mp213-215℃; 1 HNMR (500MHz, CDCl 3 ): δ=8.26(s, 1H)...

Embodiment 3

[0034] Example 3: Synthesis of 5-phenylbenzofluorenone using 3-phenyl-1-(2'-o-methylphenylethynyl)phenyl-2-allyl ketone as raw material

[0035]

[0036] Add 0.2mmol of 3-phenyl-1-(2'-o-methylphenylethynyl)phenyl-2-allyl ketone, 0.016mmol of Pd / C and 0.4mmol of N-fluoropyridine trifluoromethanesulfonate to 10mL in sequence In a pressure-proof airtight container, add 2.0 mL of dichloromethane. Stir the reaction at room temperature, TLC follow-up detection, after 3 hours of reaction, the reaction solution is diluted with 10mL of dichloromethane, filtered to obtain the clear liquid, and the solvent is removed by column chromatography (eluent ratio: sherwood oil to acetic acid Ethyl ester (volume ratio 15:1) was separated, the eluate was collected, and the solvent was distilled off to obtain 5-o-methylphenylbenzofluorenone as an orange solid with a yield of 70%.

[0037] Orange solid; mp213-215℃; 1 HNMR (500MHz, CDCl 3 ): δ=8.26(s, 1H), 8.00-7.96(m, 1H), 7.76(dd, J 1 =6.0Hz,J...

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Abstract

The invention relates to an organic compound synthetic method and provides a method for preparing a benzfluorenone compound by palladium as a catalyst. The method solves the problem that the existing benzfluorenone compound synthesis method utilizes difficultly prepared raw materials and has a high reaction temperature, a lot of reaction processes, a low yield and long reaction time. The method comprises that o-alkynylchalcone as a raw material and a fluoride reagent as an oxidizing agent undergo a reaction in the presence of a palladium compound as a catalyst to produce the benzfluorenone compound shown in the structural formula (II). The method utilizes a base metal to replace an expensive precious metal and realizes a reaction under mild conditions. The reaction formula is shown in the following description.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for preparing benzofluorenone compounds using palladium as a catalyst. Background technique [0002] Fluorenone is a variety of fine chemical raw materials, mainly used in functional polymers, and can also be used in medicine, pesticides, dyes, etc. Benzofluorenone and its derivatives are a common type of fluorenone, which has a unique position in the field of life sciences, optoelectronic materials and dye industries, and has special properties that other fluorenones do not have (such as: adding benzofluorenone Ketone resin can increase its strength). [0003] The traditional method for synthesizing fluorenone is through the oxidation of fluorene. This method has poor substrate availability and produces a large amount of organic or inorganic waste. In recent years, some new methods of synthesizing fluorenones have also been developed: (1) Friedel-Crafts r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/67C07C49/665C07C49/697C07C49/753C07C49/683
Inventor 刘运奎张剑吴德贵
Owner HUAWEI TEHCHNOLOGIES CO LTD
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