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Synthetic method for cyclopropyl diphenyl sulfonium trifluoromethanesulfonic salt

A technology of cyclopropyl diphenyl sulfonium and trifluoromethanesulfonate is applied in the synthesis field of sulfur ylide reagent, can solve the problems of complex synthesis process, difficult to be widely used and the like, and achieves high yield, easy operation and reaction conditions mild effect

Active Publication Date: 2017-04-26
河北桑迪亚医药技术有限责任公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to provide a kind of synthetic method of cyclopropyl diphenylsulfonium trifluoromethanesulfonate, to solve the complex process of cyclopropyl diphenylsulfonium tetrafluoroborate in the prior art as sulfur ylide reagent synthesis process and difficult to apply widely

Method used

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  • Synthetic method for cyclopropyl diphenyl sulfonium trifluoromethanesulfonic salt
  • Synthetic method for cyclopropyl diphenyl sulfonium trifluoromethanesulfonic salt
  • Synthetic method for cyclopropyl diphenyl sulfonium trifluoromethanesulfonic salt

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Embodiment 1

[0030] (a) Synthesis of 3-bromopropyl trifluoromethanesulfonate: 13.9g (0.10mol) 3-bromopropanol, 8.7g (0.11mol) pyridine and 150mL dichloromethane were added in a 250mL three-necked flask, cooled to 0°C. Slowly add 29.63 g (0.105 mol) of trifluoromethanesulfonic anhydride dropwise under the conditions of stirring and temperature at -20°C. After the dropwise addition, the temperature is naturally raised to room temperature and reacted overnight. After the reaction finishes, add 30mL concentration to the reaction solution and be the dilute hydrochloric acid of 0.1mol / L, stir and separate layers, extract the organic phase, then wash the organic phase with 0.1mol / L sodium carbonate aqueous solution and saturated sodium chloride aqueous solution respectively, The organic phase was dried with anhydrous sodium sulfate and concentrated to obtain 22 g of 3-bromopropyl triflate with a yield of 81%.

[0031] The reaction formula is as follows:

[0032]

[0033] (b) Synthesis of 3-b...

Embodiment 2

[0041] Cyclopropyldiphenylsulfonium trifluoromethanesulfonate was synthesized according to the following steps, and the synthetic route was the same as in Example 1.

[0042] (a) Synthesis of 3-chloropropyl trifluoromethanesulfonate: 9.5g (0.10mol) 3-chloropropanol, 11.2g (0.11mol) triethylamine and 100mL chloroform were added in a 250mL three-necked flask, cooled to 0°C. 31.2 g (0.11 mol) of trifluoromethanesulfonic anhydride was slowly added dropwise at a temperature of -10° C. After the dropwise addition, the temperature was naturally raised to room temperature and reacted overnight. After the reaction finishes, add 30mL concentration to the reaction solution and be the dilute hydrochloric acid of 0.1mol / L, stir and separate layers, extract the organic phase, then wash the organic phase with 0.1mol / L sodium carbonate aqueous solution and saturated sodium chloride aqueous solution respectively, The organic phase was dried with anhydrous sodium sulfate and concentrated to ob...

Embodiment 3

[0046] Cyclopropyldiphenylsulfonium trifluoromethanesulfonate was synthesized according to the following steps, and the synthetic route was the same as in Example 1.

[0047] (a) Synthesis of 3-iodopropyl trifluoromethanesulfonate: 25g (0.134mol) 3-iodopropanol, 26g (0.202mol) diisopropylethylamine and 150mL 1,2-dichloroethyl Thane was added into a 250mL three-necked flask, and the temperature was lowered to 0°C. 56.9 g (0.202 mol) of trifluoromethanesulfonic anhydride was slowly added dropwise under stirring at a temperature of 0° C. After the dropwise addition, the temperature was naturally raised to room temperature and reacted overnight. After the reaction finishes, add 30mL concentration to the reaction solution and be the dilute hydrochloric acid of 0.1mol / L, stir layering, extract the organic phase, then wash the organic phase with 0.1mol / L sodium carbonate aqueous solution and saturated sodium chloride aqueous solution respectively, The organic phase was dried with an...

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Abstract

The invention provides a synthetic method for cyclopropyl diphenyl sulfonium trifluoromethanesulfonic salt. The synthetic method includes the steps that (a) 3-halogen-1-propyl alcohol and trifluoromethanesulfonic anhydride serve as raw materials for synthesizing 3-halogenation propyl trifluoromethanesulfonate; (b) the 3-halogenation propyl trifluoromethanesulfonate and diphenyl sulfide are reacted for synthesizing 3-halogenation propyl diphenyl sulfonium trifluoromethanesulfonic salt; (c) the 3-halogenation propyl diphenyl sulfonium trifluoromethanesulfonic salt and strong base are reacted for synthesizing the cyclopropyl diphenyl sulfonium trifluoromethanesulfonic salt. According to the cyclopropyl diphenyl sulfonium trifluoromethanesulfonic salt, the synthetic method is easy to operate, the reaction condition is mild, the yield is high, and amplification is easy; the cyclopropyl diphenyl sulfonium trifluoromethanesulfonic salt prepared with the method can be used for a novel sulfur ylide reagent, is used for the quaternary-cyclic-ketone synthetic process with aldehyde or ketone as a substrate, the activity of the yclopropyl diphenyl sulfonium trifluoromethanesulfonic salt is similar to the activity of a common traditional sulfur ylide reagent-cyclopropyl diphenyl sulfonium tetrafluoroborate, and broad application prospects are achieved.

Description

technical field [0001] The invention relates to a synthesis method of sulfur ylide reagent, in particular to a synthesis method of cyclopropyldiphenylsulfonium trifluoromethanesulfonate. Background technique [0002] Cyclopropylthio ylide reagent is a key reagent for the synthesis of four-membered ring ketones through aldehydes or ketones. In traditional methods, cyclopropyldiphenylsulfonium tetrafluoroborate is usually used as cyclopropylthio ylide reagent, but this Reagents are expensive and not available in large quantities in the market. This is mainly due to the fact that silver tetrafluoroborate is an expensive and highly deliquescent reagent, which makes the synthesis process of cyclopropyldiphenylsulfonium tetrafluoroborate complex and difficult, which limits the use of this reagent in the laboratory. And widely used in large-scale production process. [0003] Cyclopropyldiphenylsulfonium triflate has a photobleaching effect, and it is commonly used as a photoacid ...

Claims

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Application Information

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IPC IPC(8): C07C381/12C07C45/68C07C49/697
CPCC07C45/68C07C303/28C07C303/32C07C381/12C07C309/65C07C309/06C07C49/697
Inventor 刘海涛杨欣韩玉朝茹庆科何雷夏俊义郎恒元
Owner 河北桑迪亚医药技术有限责任公司
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