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A kind of catalytic synthesis method of aryl sulfide compound

A synthetic method and technology of aryl sulfide, which is applied in the synthesis of pharmaceutical intermediates and the field of organic synthesis, can solve problems such as the need to expand the scope of substrates, take a long time, and the reaction yield is not high enough, and achieve the effect of wide market value and production potential

Active Publication Date: 2016-12-28
菏泽市金沃泰化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] As mentioned above, a variety of synthetic methods of aryl sulfide compounds are disclosed in the prior art, but these methods in the prior art still have the problems of insufficient reaction yield, long time-consuming, and the need to expand the scope of substrates

Method used

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  • A kind of catalytic synthesis method of aryl sulfide compound
  • A kind of catalytic synthesis method of aryl sulfide compound
  • A kind of catalytic synthesis method of aryl sulfide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037]

[0038] At room temperature, in an appropriate amount of organic solvent benzyl nitrile, add 100mmol of the above formula (I) compound, 150mmol of the above formula (II) compound and 200mmol of the above formula (III) compound, then add 5mmol of catalyst (for 2mmol Pd(TFA) 2 and 3mmol Rh(cod) 2 BF 4 mixture), 21mmol accelerator (a mixture of 7mmol zinc iodide and 14mmol copper trifluoromethanesulfonate) and 50mmol base N-methylmorpholine, then the temperature was raised to 60°C, and the reaction was stirred at this temperature for 8 hours.

[0039]After the reaction, filter the reaction system, add saturated brine to the filtrate, shake fully, then add ethyl acetate to extract 2-3 times, combine the organic phases, dry over anhydrous sodium sulfate, concentrate under reduced pressure, and filter the obtained residue over 300-400 mesh silica gel column chromatography, using an equal volume of acetone and ethyl acetate mixture as eluent, to obtain the compound of for...

Embodiment 2

[0042]

[0043] At room temperature, in an appropriate amount of organic solvent benzyl nitrile, add 100mmol of the above formula (I) compound, 170mmol of the above formula (II) compound and 250mmol of the above formula (III) compound, then add 7mmol of catalyst (2.55mmol Pd (TFA) 2 and 4.45mmol Rh(cod) 2 BF 4 mixture), 27mmol accelerator (a mixture of 9mmol zinc iodide and 18mmol copper trifluoromethanesulfonate) and 65mmol base N-methylmorpholine, then heated to 70°C, and stirred at this temperature for 6 hours.

[0044] After the reaction, filter the reaction system, add saturated brine to the filtrate, shake fully, then add ethyl acetate to extract 2-3 times, combine the organic phases, dry over anhydrous sodium sulfate, concentrate under reduced pressure, and filter the obtained residue over 300-400 mesh silica gel column chromatography, using equal volumes of acetone and ethyl acetate mixture as eluent, to obtain the compound of formula (IV) with a yield of 98.2%.

...

Embodiment 3

[0047]

[0048] At room temperature, in an appropriate amount of organic solvent benzyl nitrile, add 100mmol of the above formula (I) compound, 200mmol of the above formula (II) compound and 300mmol of the above formula (III) compound, then add 10mmol of catalyst (3.34mmol Pd (TFA) 2 and 6.66mmol Rh(cod) 2 BF 4 mixture), 30mmol accelerator (a mixture of 10mmol zinc iodide and 20mmol copper trifluoromethanesulfonate) and 80mmol base N-methylmorpholine, then the temperature was raised to 80°C, and the reaction was stirred at this temperature for 5 hours.

[0049] After the reaction, filter the reaction system, add saturated brine to the filtrate, shake fully, then add ethyl acetate to extract 2-3 times, combine the organic phases, dry over anhydrous sodium sulfate, concentrate under reduced pressure, and filter the obtained residue over 300-400 mesh silica gel column chromatography, using an equal volume of acetone and ethyl acetate mixture as eluent to obtain the compound o...

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Abstract

The invention provides a catalytic synthetic method for an aryl sulfide compound shown in a formula (IV). The method comprises: in an organic solvent, in the presence of a catalyst, an accelerant and alkali, carrying out a reaction on a compound shown in a formula (I), a compound shown in a formula (II) and a compound shown in a formula (III) so as to obtain the compound shown in the formula (IV). The formula (IV) is shown in the description, wherein R is H, C1-C6 alkyl, C1-C6 alkoxyl or halogen; n is an integer of 1-4. The method comprehensively selects and coordinates the catalyst, the accelerant, the alkali, the organic solvent and the like so as to obtain a target product with a high yield, thereby providing a brand new method for synthesis of the compounds and developing a novel synthetic channel for the field of chemical industry and medicines. The method has wide market value and potential productivity.

Description

technical field [0001] The invention relates to a method for synthesizing sulfur compounds, more specifically to a method for catalytically synthesizing aryl sulfide compounds, and belongs to the technical field of organic synthesis, especially the field of pharmaceutical intermediate synthesis. Background technique [0002] The thioether structure is an important building block in natural products, pharmaceutical compounds, and functional materials, which endows these molecules with various functions and modifiable properties. With the in-depth research on the functionalization reaction of C-H bonds, the research team on the construction of C-S bonds is also growing. The development of novel and effective C-S bond formation strategies is of great significance to the fields of synthesis and materials. [0003] The existing reported methods often use various types of thiolating reagents to realize the thiolation of C-H bonds, such as disulfides, sulfonyl hydrazides, sulfonyl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C319/14C07C323/20C07C321/28C07C323/09
Inventor 王栩
Owner 菏泽市金沃泰化工有限公司