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Method for catalyzing and synthesizing benzil derivatives from alkali type copper fluoride

A technology of copper fluoride and compounds, which is applied in the field of benzil derivatives catalyzed by basic copper fluoride, can solve the problems of complicated preparation steps, difficult separation and purification, harsh temperature, etc., and achieves mild reaction conditions, simple operation, The effect of low toxicity

Active Publication Date: 2013-09-04
YANGZHOU JUNRUI CHUANGZHI IND DESIGN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

(3) The oxygen source used is relatively expensive (see Xu, C.-F. et al. Org. Lett., 2011, 13, 1556; Sawama, Y. et al. Eur. J. Org. Chem., 2011, 3361)
However, the preparation steps of this method are complicated, the temperature is harsh (100-230 ° C), the time is long (it takes several days), and in addition, special anti-corrosion containers are required due to the use of highly toxic and dangerous hydrogen fluoride reagents; in addition, in the preparation Cu 3 (OH) 2 f 4 Difficulty in separation and purification

Method used

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  • Method for catalyzing and synthesizing benzil derivatives from alkali type copper fluoride
  • Method for catalyzing and synthesizing benzil derivatives from alkali type copper fluoride
  • Method for catalyzing and synthesizing benzil derivatives from alkali type copper fluoride

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Experimental program
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Embodiment 1

[0033]

[0034] (1) Mix Cu powder (64mg, 1mmol), 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane di(tetrafluoroborate) salt (Selectfluor, 354.3mg, 1mmol), was added to a 200mL round bottom flask, and then 10mL of acetonitrile / water (V:V=50:1) was added as a solvent. Then, magnetically stirred at room temperature for 1 h to obtain a light blue solution and a white precipitate. Filter to remove the white precipitate, concentrate the mother liquor, and precipitate 75 mg of basic copper fluoride, with a yield of 75%.

[0035] Characterization data of FCuOH: IR:ν3150(OH)cm -1 ; 19 F NMR (376MHz, CD 3 CN):δ-151.06ppm;ESI-MS:m / z:80[M-F] + .

[0036] (2) Add 35.6mg (0.2mmol) toluene, 141.7mg (0.4mmol) Selectfluor, 1mg (0.01mmol) FCuOH to a 10mL round bottom flask, then add 2mL acetonitrile / water (V:V=50:1 ) as a solvent. Then, the mixture was magnetically stirred for 4 h at room temperature. Then, 10 g of column chromatography silica gel (100-200 mesh) was added to th...

Embodiment 2

[0039] In step (1), Selectfluor was changed to 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane di(hexafluorophosphate) salt (470.6mg, 1mmol), and other operations were the same Example 1, 74 mg of basic copper fluoride was obtained, with a yield of 74%.

[0040] In step (2), the amount of basic copper fluoride was changed to 0.6 mg (0.006 mmol), and the other operations were the same as in Example 1 to obtain benzil with a yield of 77%.

Embodiment 3

[0042] In step (1), Selectfluor was changed to 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane di(trifluoromethanesulfonate) salt (478.8mg, 1mmol), others The operation was the same as in Example 1, and 72 mg of basic copper fluoride was obtained, with a yield of 72%.

[0043] In step (2), the amount of basic copper fluoride was changed to 2 mg (0.02 mmol), and other operations were the same as in Example 1 to obtain benzil with a yield of 82%.

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Abstract

The invention provides a method for catalyzing and synthesizing benzil derivatives from alkali type copper fluoride: diphenyl acetylene compounds shown in formula I is the raw material, alkali type copper fluoride is the catalyst, selectflour is the oxidizing agent, mixing acetonitrile and water according to volume ratio of 5-500 to 1 and string the mixture to react at room temperature for 1 to 24 hours, so as to obtain the benzil derivatives shown in formula II by post processing and preparing of the reaction liquid after reaction; and alkali type copper fluoride is prepared by mixing copper powder, 1-Chloromethyl-4-fluoro-1 and 4 - dinitrogen mixed double loop (2.2.2) octane salt and reacting under the action of the mixed solution of organic solvent and water. The method provided by the invention has the advantages that the catalyst is low in cost and toxicity, the oxygen source is easy to get and environmental friendly, the reaction condition is moderate, the functional group universality is good, and the operation is simple and convenient.

Description

(1) Technical field [0001] The invention relates to a method for catalytically synthesizing benzil derivatives with basic copper fluoride. (2) Background technology [0002] Benzil and its derivatives are a special class of organic compounds with extremely wide applications. They can be used as an auxiliary heat stabilizer to overcome the serious shortage of weather resistance of the original metal soap stabilizers, thus greatly expanding the application range of metal soap stabilizers; they can also be combined with a variety of stabilizers The synergistic effect between components and components can effectively improve the thermal stability of plastic products and other properties; its complex with rare earth ions as a catalyst can solve the problem of long-chain branching of traditional catalysts in the synthesis of high molecular weight polyethylene. It can also be used to synthesize imidazoles, benzopyrazines and other drug intermediates with anti-tumor activity. In a...

Claims

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Application Information

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IPC IPC(8): C07C49/784C07C49/813C07C45/27B01J27/122
Inventor 刘运奎张文霞张剑徐振元
Owner YANGZHOU JUNRUI CHUANGZHI IND DESIGN
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