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A kind of preparation method of thioether compound and product thereof

A compound and sulfide technology, applied in the preparation of sulfides, steroids, organic chemistry, etc., can solve the problems of large amount of metal usage, long reaction time and high temperature, and achieve the elimination of metal residues, good biological activity of products, and high production efficiency. high rate effect

Inactive Publication Date: 2018-10-19
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The traditional C-S bond and C-O bond construction method, that is, the Ullmann reaction, even after years of improvement, still has the disadvantages of using metal catalysis, large amount of metal used, high temperature, and long reaction time; and some transition Metal-catalyzed reactions to generate new C-S bonds and C-O bonds, such as the method reported by Buchwald et al., still inevitably use noble metals and high-priced organophosphine ligands

Method used

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  • A kind of preparation method of thioether compound and product thereof
  • A kind of preparation method of thioether compound and product thereof
  • A kind of preparation method of thioether compound and product thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0044]

[0045] In a pre-dried 5mL round-bottomed flask, under the protection of argon, add acetonitrile (2mL) and diphenylsulfoxide (44.5mg, 0.22mmol) successively, cool down to 0°C, and slowly add trifluoromethanesulfonic anhydride (40.8μL , 0.24mmol), added 2-hydroxy-7-bromonaphthalene (44.6mg, 0.2mmol) and stirred at 500rpm at this temperature for 3h. Potassium phosphate (188.7 mg, 0.44 mmol) was added, heated to 70° C., and stirred at 500 rpm for 24 hours.

[0046] After the reaction solution was stirred, it was washed with water, extracted three times with dichloromethane, and the organic phases extracted several times were combined into a 100mL eggplant-shaped flask, using a Heidolph rotary evaporator with a rotation speed of 120rpm, a temperature of 38°C, and a vacuum of 0.1Mpa , treated for 3 min, and then performed column chromatography using 200-mesh column chromatography silica gel, and the developing solvent was petroleum ether:ethyl acetate=99:1, and the targe...

Embodiment 2

[0050]

[0051] In a pre-dried 5mL round-bottomed flask, under the protection of argon, add acetonitrile (2mL) and diphenylsulfoxide (44.5mg, 0.22mmol) successively, cool down to 0°C, and slowly add trifluoromethanesulfonic anhydride (40.8μL , 0.24mmol), added 2-hydroxy-6-cyanonaphthalene (33.9mg, 0.2mmol), stirred at 600rpm at this temperature for 3h. Potassium phosphate (188.7 mg, 0.88 mmol) was added, heated to 70° C., and stirred at 600 rpm for 24 hours.

[0052] After the reaction solution was stirred, it was washed with water, extracted three times with dichloromethane, and the organic phases extracted several times were combined into a 100mL eggplant-shaped flask, using a Heidolph rotary evaporator with a rotation speed of 200rpm, a temperature of 38°C, and a vacuum of 0.1Mpa , treated for 4min, and then carried out column chromatography using 200-mesh column chromatography silica gel, and the developer was petroleum ether:ethyl acetate=99:1, and the target compound ...

Embodiment 3

[0056]

[0057] In a pre-dried 5mL round bottom flask, under the protection of argon, add acetonitrile (2mL), 4-methylphenyl-n-hexyl sulfoxide (49.4mg, 0.22mmol) successively, cool down to 0°C, and slowly add trifluoro Add methanesulfonic anhydride (40.8 μL, 0.24 mmol), add 2-hydroxynaphthalene (28.9 mg, 0.2 mmol), and stir at 700 rpm for three hours at this temperature. Potassium phosphate (188.7 mg, 0.88 mmol) was added, heated to 70° C., and stirred at 700 rpm for 24 hours.

[0058] After the reaction solution was stirred, it was washed with water, extracted three times with dichloromethane, and the organic phases extracted several times were combined into a 100mL eggplant-shaped flask, using a Heidolph rotary evaporator with a rotation speed of 200rpm, a temperature of 38°C, and a vacuum of 0.1Mpa , the treatment time was 3min, and then 200 mesh column chromatography silica gel was used for column chromatography, and the developer was petroleum ether:ethyl acetate=99:1,...

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Abstract

The invention discloses a preparation method of a thioether compound and a product of the sulfoether compound. The method comprises the following steps: adding a sulfoxide compound into acetonitrile or dichloromethane under the protection of gas which does not react with a substrate, cooling the mixture, then adding trifluoromethanesulfonic anhydride or trifluoroacetic anhydride, adding an arylphenol compound, keeping the temperature and stirring for 2 to 4 hours, adding potassium phosphate, heating to 65 to 75 DEG C, stirring for 20 to 28 hours, and carrying out extraction and concentration chromatography to obtain a target product. The method for preparing the sulfoether compound has the characteristics of simplicity, efficiency, mildness and economy.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a preparation method of thioether compounds and products thereof. Background technique [0002] The Ullmann reaction was first reported in 1901, and it is one of the effective methods for constructing C-C bonds, C-N bonds, C-O bonds and C-S bonds in organic synthesis. The efficient and high-yield synthesis of biphenyl and its derivatives through the Ullmann reaction has always been one of the research hotspots in organic synthesis. The products obtained by Ullmann coupling reaction widely exist in some natural products with physiological activity, such as biflavone and so on. At the same time, this reaction is also used in organic synthesis, medicine, agricultural supplies, commercial dyes, organic conductors and organic semiconductors. [0003] The traditional C-S bond and C-O bond construction method, that is, the Ullmann reaction, even after years of i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C319/14C07C323/21C07C323/62C07J31/00
CPCC07C319/14C07J31/003C07C323/21C07C323/62
Inventor 黄申林尹太玉陈登峰冯庆源
Owner NANJING FORESTRY UNIV
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