Preparation method of sulfone compound
A technology of compounds and sulfones, which is applied in the field of preparation of sulfones, can solve problems such as limiting synthetic applications, achieve broad industrial application value, mild reaction conditions, and simple operation
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[0026] The method for preparing a sulfone compound includes the following steps:
[0027] a) Disperse the sulfonyl hydrazide with structure (I) in the cycloalkane solvent with structure (II);
[0028]
[0029] b) Add an iron salt catalyst and a peroxide oxidizer to the mixture obtained in step a), and react at a temperature of 90-130°C for 6-12 hours to obtain a sulfone compound containing structure (III);
[0030]
[0031] When the R is an aryl group, the aryl group is phenyl or naphthyl;
[0032] When the R is a substituted aryl group, the substituted aryl group is p-chlorophenyl, p-tolyl, 2,4,6-trimethylphenyl, p-methoxyphenyl, m-methoxyphenyl , O-methoxyphenyl, p-trifluoromethylphenyl, p-tert-butylphenyl, p-fluorophenyl, p-iodophenyl, 3-nitro-4-chlorophenyl, 4-methyl-3 -Fluorophenyl, p-acetamidophenyl or p-bromophenyl;
[0033] Said n is 1, 2, 3 or 4;
[0034] The iron salt is ferric chloride, ferrous sulfate, iron oxide, ferric bromide, ferric sulfate, ferric tetroxide, ferrous ch...
Example Embodiment
[0041] Example 1
[0042] In a clean and dry 10 ml Schlenk reaction tube, add 0.50 mmol p-toluenesulfonyl hydrazide, 1 ml cyclohexane, 0.025 mmol ferric chloride, and 1 mmol di-tert-butyl peroxide. Seal and react at 120°C for 6 hours. After the reaction, the reaction mixture was directly spin-dried cyclohexane in the reaction by a rotary evaporator, and the remaining residue was separated by a silica gel column using petroleum ether as the eluent, and the target product obtained was a colorless liquid, which was passed through the hydrogen nuclear magnetic resonance spectrum , Carbon spectroscopy and high-resolution mass spectrometry analysis confirmed that the target product was p-toluenecyclohexyl sulfone, and the yield was 80%.
[0043] The proton nuclear magnetic resonance spectrum of the product prepared in this example is as Figure 1a As shown, the NMR carbon spectrum is as Figure 1b As shown, the high-resolution mass spectrum is as Figure 1c Shown.
Example Embodiment
[0044] Example 2
[0045] In a clean and dry 10 ml Schlenk reaction tube, add 0.50 mmol p-toluenesulfonyl hydrazide, 1 ml cyclohexane, 0.03 mmol iron sulfate, 1 mmol di-tert-butyl peroxide, and seal the reaction tube. , React at 130°C for 10 hours. After the reaction, the reaction mixture was directly spin-dried cyclohexane in the reaction by a rotary evaporator, and the remaining residue was separated by a silica gel column using petroleum ether as the eluent, and the target product obtained was a colorless liquid, which was passed through the hydrogen nuclear magnetic resonance spectrum , Carbon spectroscopy and high-resolution mass spectrometry analysis confirmed that the target product was p-toluenecyclohexyl sulfone, and the yield was 68%.
[0046] The proton nuclear magnetic resonance spectrum of the product prepared in this example is as Figure 1a As shown, the NMR carbon spectrum is as Figure 1b As shown, the high-resolution mass spectrum is as Figure 1c Shown.
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