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Method for preparing 2-(methylsulfinyl)benzoic acid

A technology of methyl sulfinyl and benzoic acid, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of cumbersome reaction steps, high temperature, unstable corrosiveness, etc., and avoid toxic reagents. The effect of use, yield promotion, and simple operation

Active Publication Date: 2020-10-30
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is: the reaction not only needs to use the transition metal reagent ferric nitrate which is easy to deliquescence and instability, but also needs to use additional ligand additives and specific reaction vessels, and the reaction steps are cumbersome
The disadvantage of this method is that a strong acid is used and the temperature required for the reaction is higher
The disadvantage of this method is that it uses the m-chloroperoxybenzoic acid reagent which is corrosive and unstable and needs to be stored at low temperature, and also uses toxic chloroform as the reaction solvent

Method used

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  • Method for preparing 2-(methylsulfinyl)benzoic acid
  • Method for preparing 2-(methylsulfinyl)benzoic acid
  • Method for preparing 2-(methylsulfinyl)benzoic acid

Examples

Experimental program
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Effect test

specific Embodiment 1

[0018] Specific Example 1: Add methanol (30mL), 2-(methylthio)benzoic acid (6mmol, 1.01g), 1-chloromethyl-4-fluoro-1,4- Diazabicyclo[2.2.2]octane bis(tetrafluoroborate) salt [Selectfluor] (6mmol, 2.13g), the reaction temperature was controlled at 20 degrees Celsius, and the reaction was vigorously stirred for 24 hours. After the reaction was completed, the reaction solution was filtered, concentrated, and dried to obtain the target product 2-(methylsulfinyl)benzoic acid (1.05 g, 95%). The equations involved in the reaction are as follows:

[0019]

[0020] The NMR data and mass spectrum data of the target product 2-(methylsulfinyl)benzoic acid are as follows:

[0021] 1 H NMR (300MHz, DMSO) δ8.15–8.13(m,1H),8.07–8.04(m,1H),7.92(t,J=7.4Hz,1H),7.67(t,J=7.5Hz,1H) ,2.75(s,3H).

[0022] 13 C NMR (75MHz, DMSO) δ167.01, 150.76, 134.23, 131.33, 130.87, 127.85, 123.95, 44.41.

[0023] LCMS(ESI,m / z):185.00[M+H] + .

specific Embodiment 2

[0024] Specific Example 2: Add acetonitrile (30mL), 2-(methylthio)benzoic acid (6mmol, 1.01g), 1-chloromethyl-4-fluoro-1,4- Diazabicyclo[2.2.2]octane bis(tetrafluoroborate) salt [Selectfluor] (6mmol, 2.13g), the reaction temperature was controlled at 20 degrees Celsius, and the reaction was vigorously stirred for 24 hours. After the reaction, the reaction solution was filtered, concentrated, and dried to obtain the target product 2-(methylsulfinyl)benzoic acid (0.17 g, 15%). The equations involved in the reaction are as follows:

[0025]

specific Embodiment 3

[0026] Specific Example 3: Add methanol (30mL), 2-(methylthio)benzoic acid (6mmol, 1.01g), 1-chloromethyl-4-fluoro-1,4- Diazabicyclo[2.2.2]octane bis(tetrafluoroborate) salt [Selectfluor] (3mmol, 1.06g), the reaction temperature was controlled at 20 degrees Celsius, and the reaction was vigorously stirred for 24 hours. After the reaction was completed, the reaction solution was filtered, concentrated, and dried in sequence, but the target product 2-(methylsulfinyl)benzoic acid was not isolated. The equations involved in the reaction are as follows:

[0027]

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Abstract

The invention relates to the technical field of fine chemical engineering, and discloses a method for preparing 2-(methylsulfinyl)benzoic acid. The method comprises the specific steps: by taking 2-(methylthio)benzoic acid as a reaction raw material and 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane bis(tetrafluoroborate) salt as an additive, carrying out a reaction in a methanol solvent atthe temperature of 20 DEG C for 24 hours, filtering a reaction solution after the reaction is finished, carrying out reduced pressure distillation, and collecting to obtain the target product 2-(methylsulfinyl)benzoic acid. The method is simple and convenient to operate, 2-(methylthio)benzoic acid is used as a reaction raw material, the target product is efficiently synthesized in one step, the use of a toxic reagent chloroform, an acid with strong corrosivity and a transition metal salt is avoided, and the method has potential application value.

Description

technical field [0001] The invention belongs to the field of fine chemical industry and relates to a method for preparing 2-(methylsulfinyl)benzoic acid. Background technique [0002] 2-(Methylsulfinyl)benzoic acid is an important class of organic compounds. Its parent skeleton, benzoic acid, widely exists in natural products and has good antifungal and food antiseptic activities. At the same time, this type of compound is an important organic compound. Synthetic intermediates are of great value in the preparation of biological and medical related materials. Therefore, how to directly and efficiently synthesize 2-(methylsulfinyl)benzoic acid has attracted great attention of chemists. The synthetic method of 2-(methylsulfinyl) benzoic acid is seldom reported at present, mainly contains following three kinds: [0003] The first method uses 2-(methylthio)benzoic acid as a raw material, acetonitrile as a solvent, and activates the thioether bond by means of a catalytic system ...

Claims

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Application Information

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IPC IPC(8): C07C315/02C07C317/44
CPCC07C315/02C07C317/44
Inventor 李义戴胜飞李正义孙小强杨科
Owner CHANGZHOU UNIV
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