A kind of preparation method of symmetrically substituted sulfonate compound
A technology for sulfonate esters and compounds, which is applied in the field of preparation of sulfonate ester compounds, can solve problems such as limiting synthetic applications, and achieve the effects of broad industrial application value, mild reaction conditions, and simple operation
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[0018] The preparation method of a symmetrically substituted sulfonate compound comprises the following steps:
[0019] Disperse the sulfonyl hydrazide with the structure (I) in an ester solvent, add the catalyst 1,4-benzenediol, and then heat with stirring to obtain the sulfonate compound of the present invention with the structure (II):
[0020]
[0021] Wherein, R is aryl, substituted aryl, heteroaryl or alkyl;
[0022] R is an aryl group, and the aryl group is phenyl or naphthyl; R is a substituted aryl group, and 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, p-bromobenzene R is a heteroaryl group, and the heteroaryl group is 2-furyl, 2-thienyl; R is an alkyl group, and the alkyl group is benzyl, n-octyl, n-butyl, n-decyl Octyl or n-hexyl;
[0023] The ester solvent is ethyl acetate, methyl acetate, butyl aceta...
Embodiment 1
[0028] In a clean and dry 100ml round bottom flask, add 10mmol of p-toluenesulfonyl hydrazide, 1mmol of 1,4-benzenediol, and 20ml of ethyl acetate in sequence, install a reflux condenser, and place the oil at 80°C React in the bath for 15 hours. After the reaction, the solvent ethyl acetate in the reaction mixture was removed by rotary evaporation, and the remaining mixture was separated by silica gel column with petroleum ether and ethyl acetate as eluent, and the target product obtained was a white solid, which was obtained by NMR. Resonance hydrogen spectrum and carbon spectrum analysis confirmed that the target product was S-p-tolylthio-p-tolyl sulfone, and the yield was 80%.
[0029] The proton nuclear magnetic resonance spectrum of the product prepared in this embodiment is as follows: Figure 1a As shown, the carbon NMR spectrum is shown as Figure 1b shown.
Embodiment 2
[0031] In a clean and dry 100ml round bottom flask, add 15mmol of p-toluenesulfonyl hydrazide, 2mmol of 1,4-benzenediol, and 25ml of butyl acetate successively, install a reflux condenser, and place in the oil at 110°C React in a bath for 12 hours. After the reaction was over, the solvent butyl acetate in the reaction mixture was removed by distillation under reduced pressure, and then the remaining mixture was separated by silica gel column with sherwood oil and ethyl acetate as eluent, and the target product obtained was a white solid. H NMR and C NMR analysis confirmed that the target product was S-p-tolylthio-p-tolylsulfone with a yield of 88%.
[0032] The proton nuclear magnetic resonance spectrum of the product prepared in this embodiment is as follows: Figure 1a As shown, the carbon NMR spectrum is shown as Figure 1b shown.
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