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Method for preparing β-ketosulfone or β-hydroxysulfone by reaction of substituted alkenes and sulfonyl hydrazide derivatives

A technology of sulfonyl hydrazide and derivatives, applied in the field of organic chemical synthesis, to achieve the effects of easy preparation, simple process and cheap raw materials

Active Publication Date: 2020-06-09
JIANGXI MENHOVER CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This type of reaction combining visible light catalysis and air as oxidant has not been reported

Method used

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  • Method for preparing β-ketosulfone or β-hydroxysulfone by reaction of substituted alkenes and sulfonyl hydrazide derivatives
  • Method for preparing β-ketosulfone or β-hydroxysulfone by reaction of substituted alkenes and sulfonyl hydrazide derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Add 2ml of solvent ethanol, 0.093g (0.5mmol) of p-toluenesulfonyl hydrazide, 0.156g (1.5mmol) of styrene, 0.112g (1mmol) of base triethylenediamine, and 3.2mg of photocatalyst methylene blue in a 10ml reaction tube. (0.01mmol), irradiated with 12W blue LED, exposed to normal temperature reaction. Follow the reaction until the complete disappearance of p-toluenesulfonyl hydrazide. After the reaction, it was extracted three times with water and ethyl acetate. The aqueous layer was removed, and the organic layer was dried over anhydrous sodium sulfate. The solvent was removed by a rotary evaporator, and then purified by silica gel chromatography (ethyl acetate / petroleum ether=1 / 10) to obtain 0.106 g of pure 2-p-toluenesulfonylacetophenone with a yield of 78%. 1 H NMR (400MHz, CDCl 3 )δ7.97(d, J=7.7Hz, 2H), 7.78(d, J=8.1Hz, 2H), 7.64(t, J=7.3Hz, 1H), 7.50(t, J=7.6Hz, 2H) ,7.35(d,J=8.0Hz,2H),4.74(s,2H),2.46(s,3H). 13 C NMR (101MHz, CDCl 3 ) δ 188.15, 145.36, 135.82, 134....

Embodiment 2

[0020] In Reaction Example 1, the reaction was carried out in the same manner as in Example 1, except that 0.156 g (1.5 mmol) of styrene was changed to 0.275 g (1.5 mmol) of 1-bromo-4-vinylbenzene. 2-p-toluenesulfonyl-4'-bromoacetophenone, yield 89%. 1 HNMR (400MHz, CDCl 3 )δ8.02(t, J=1.8Hz, 1H), 7.91(ddd, J=7.8, 1.6, 1.0Hz, 1H), 7.80–7.71(m, 3H), 7.38(dd, J=15.3, 7.8Hz ,3H),4.70(s,2H),2.47(s,3H). 13 C NMR (101MHz, CDCl 3 ) δ 186.69, 144.92, 137.41, 132.04, 130.34, 128.55, 127.98, 123.18, 63.98.

Embodiment 3

[0022] In Reaction Example 1, the reaction was carried out in the same manner as in Example 1, except that 0.156 g (1.5 mmol) of styrene was changed to 0.275 g (1.5 mmol) of 1-bromo-3-vinylbenzene. 2-p-toluenesulfonyl-3'-bromoacetophenone, yield 67%. 1 HNMR (400MHz, CDCl 3 )δ8.02(t, J=1.6Hz, 1H), 7.91(d, J=7.8Hz, 1H), 7.76(t, J=6.9Hz, 3H), 7.38(dd, J=15.3, 7.8Hz, 3H), 4.70(s,2H), 2.47(s,3H). 13 C NMR (101MHz, CDCl 3 )δ 186.98, 145.64, 137.41, 137.12, 135.54, 132.09, 130.40, 129.95, 128.60, 128.03, 123.18, 63.68, 21.75.

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Abstract

The invention belongs to the technical field of organic chemical synthesis and specifically relates to a method for preparing beta-keto sulfone or beta-hydroxy sulfone from reaction of substituted olefin and sulfonyl hydrazine derivative. The method comprises the following steps: taking substituted olefin and sulfonyl hydrazine derivative as raw materials, taking air as an oxidizing agent and performing oxidizing addition reaction under the existence of photosensitizer and alkali and under the condition of visible light irradiation, thereby generating beta-keto sulfone or beta-hydroxy sulfone.The method provided by the invention is low in cost of raw materials, simple in process, green and safe, efficient and environment-friendly, and suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a method for preparing β-ketosulfone or β-hydroxysulfone by reacting substituted alkenes and sulfonyl hydrazide derivatives. Background technique [0002] β-ketosulfone or β-hydroxysulfone is a compound widely used in the fields of organic chemistry and polymer chemistry. Fields are useful. [0003] As a method for producing β-ketosulfone or β-hydroxysulfone, a method using a substituted olefin and a sulfonyl hydrazide as a starting material is known. But these methods mainly use copper salt, elemental iodine, iodide, bromide or strong acid as catalyst, peroxide as oxidant, and prepare products under heating conditions. Such reactions combining visible light catalysis and air as an oxidant have not been reported. Contents of the invention [0004] The object of the present invention is to provide, in the presence of photosensitizer and under th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C315/00C07C317/24C07C317/18
CPCC07C315/00C07C317/24C07C317/18
Inventor 朱纯银吴洁
Owner JIANGXI MENHOVER CHEM TECH CO LTD
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