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Aryl sulfuryl difluoroacetic salt compound, as well as preparation method and application thereof

A technology for arylsulfone-based difluoroacetate and compound, which is applied in the field of organic synthesis, can solve the problems of few reports of -difluoromethyl alcohol compounds, harsh reaction conditions, difficult preparation of reaction reagents, etc., and achieves product yield. The effect of high rate, high universality and few side effects

Active Publication Date: 2017-05-31
CHINA GATEWAY PHARMA DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Among the above methods, some need to use strong alkaline reagents such as LDA and t-BuOK, and the reaction needs to be controlled at low temperature, the reaction conditions are harsh, and some reaction reagents are difficult to prepare and expensive
A cheap, efficient, and mild method for the preparation of difluoromethylalcohols has rarely been reported so far
In addition, Xiao Jichang et al reported the preparation and application of potassium pyridylsulfone difluoroacetate in 2014 (X.-P Wang, J.-H.Lin, J.-C.Xiao and X.ZhengEur.J.Org .Chem.2014,928.), but the preparation process of this compound requires the use of precious metal ruthenium oxidant, which is expensive, and its reaction with aldehydes mainly generates difluoroalkene compounds

Method used

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  • Aryl sulfuryl difluoroacetic salt compound, as well as preparation method and application thereof
  • Aryl sulfuryl difluoroacetic salt compound, as well as preparation method and application thereof
  • Aryl sulfuryl difluoroacetic salt compound, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 1) At room temperature and normal pressure, put 2.25g (55mmol) NaH (60%) into a two-necked flask, and add 40ml DMSO. Under reflux of condensed water, 5.50 g (50 mmol) of thiophenol was slowly added dropwise, and reacted at room temperature for 1 h. Under the reflux of condensed water, 12.20 g (60 mmol) ethyl bromodifluoroacetate was slowly dropped into the mixture, and reacted at room temperature for 16 h. Saturated with NH in 50ml 4 Quench the reaction with Cl solution, extract with dichloromethane, combine the organic phases, wash with water and saturated NaCl aqueous solution successively, dry over anhydrous sodium sulfate, concentrate under reduced pressure, and separate by column chromatography to obtain the product 10.26g, yield 88%.

[0026] 2) Under normal pressure, 10.26g (40mmol) of the above-mentioned 17.60g (176mmol) CrO 3 , 50ml of acetic acid was put into the two-neck flask in turn, under the circulation of condensed water, the reaction was stirred a...

Embodiment 2

[0029]1) As described in Example 1, add 7.00 g (50 mmol) of p-methoxythiophenol, and add p-methoxythiophenol, sodium hydride, and ethyl difluorobromoacetate at a ratio of 1.0:1.1:1.2 at room temperature After reacting for 16 hours, we get 12.06g, yield 92%.

[0030] 2) As shown in Example 1, add The ratio of chromium trioxide was 1:4, the reaction was stirred at 60°C, and the reaction was monitored by TLC. After the disappearance of the raw materials, the reaction is stopped to obtain 11.91 g, yield 88%.

[0031] 3) As shown in Example 1, add The ratio of KOH is 1:1, the reaction is at room temperature, and the reaction is monitored by TLC. After the disappearance of the raw materials, the reaction is stopped to obtain 11.20 g, yield 91%.

Embodiment 3

[0033] 1) As described in Example 1, add 6.40 g (50 mmol) of p-fluorothiophenol, add p-fluorothiophenol, sodium hydride, and ethyl difluorobromoacetate at a ratio of 1.0:1.1:1.2, and react at 40°C for 16 hours, get 7.04g, yield 56%.

[0034] 2) As shown in Example 1, add The ratio of chromium trioxide was 1:4, the reaction was stirred at 60°C, and the reaction was monitored by TLC. After the disappearance of the raw materials, the reaction is stopped to obtain 6.52g, yield 82%.

[0035] 3) As shown in Example 1, add The ratio of NaOH was 1:1, the reaction was at room temperature, and the reaction was monitored by TLC. After the disappearance of the raw materials, the reaction is stopped to obtain 5.49g, yield 86%.

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Abstract

The invention discloses an aryl sulfuryl difluoroacetic salt compound, as well as a preparation method and application thereof. The aryl sulfuryl difluoroacetic salt compound reacts with aldehyde at room temperature to obtain an aryl sulfuryl substituted alpha-difluoromethyl alcohol compound. The aryl sulfuryl difluoroacetic salt compound has the beneficial effects of mild reaction condition, high product yield, few side effect and high universality when the aryl sulfuryl difluoroacetic salt compound is adopted to prepare the aryl sulfuryl substituted alpha-difluoromethyl alcohol compound.

Description

technical field [0001] The invention relates to an arylsulfone-based difluoroacetate compound, a preparation method and an application thereof, and belongs to the technical field of organic synthesis. Background technique [0002] Due to the unique physical and chemical properties of fluorine atoms, the introduction of fluorine atoms or fluorine-containing groups into molecules can significantly change the physiological activity of the original molecules. At present, about 30% of new drug molecules and 30-40% of pesticide molecules contain fluorine atoms or fluorine-containing functional groups. Difluoromethyl (CF 2 H) has a strong electron-withdrawing induction effect, and hydroxymethyl (CH 2 OH) has equal polarity and isostericity, and is also a lipophilic hydrogen bond donor, which makes difluoromethyl compounds of great significance in the design of life sciences, pharmacy and agrochemicals, and material development. The structural unit of α-difluoromethyl alcohol wid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/44C07C315/04C07C317/18
CPCC07C315/02C07C315/04C07C317/44C07C319/14C07C317/18C07C323/52
Inventor 刘振江朱钰君雷忠良卞明杨志强黄大康朱风群岳朝颖
Owner CHINA GATEWAY PHARMA DEV CO LTD
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