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A kind of synthetic method of aryl sulfinate compound

A technology of aryl sulfinate and synthesis method, applied in the direction of organic chemistry, etc., can solve problems such as difficulty, irritating odor, etc., and achieve the effect of reducing emission and high economy

Active Publication Date: 2021-08-24
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, sulfur dioxide is usually gaseous, has a pungent odor, and has relatively stable chemical properties. It is very difficult to directly react sulfur dioxide with organic matter.

Method used

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  • A kind of synthetic method of aryl sulfinate compound
  • A kind of synthetic method of aryl sulfinate compound
  • A kind of synthetic method of aryl sulfinate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Under nitrogen protection, p-methylphenyltetrafluoroborate diazonium salt 1a (0.2 mmol), DABSO (0.2 mmol), methanol 2a (3 mL), cuprous iodide (10 mol%), azobisisobutyronitrile (AIBN, 10 mol%) was added to a Schlenk reaction tube and sealed. Heated to 80°C and the reaction time was over 10 hours. After the reaction, the solvent was removed under reduced pressure, and the target product 3a was obtained by column chromatography with a yield of 72%. 1 H NMR (400MHz, CDCl 3 ):δ7.57(d,J=8.0Hz,2H),7.32(d,J=8.0Hz,2H),3.44(s,3H), 2.41(s,3H). 13 C NMR (101MHz, CDCl 3 ): 142.8, 140.8, 129.7, 125.3, 49.3, 21.4.

Embodiment 2

[0029] Under nitrogen, p-methylphenyltetrafluoroborate diazonium salt 1a (0.2 mmol), DABSO (0.24 mmol), ethanol 2b (3 mL), cuprous bromide (10 mol%), benzoyl peroxide ( BPO, 5 mol%) was added to the Schlenk reaction tube and sealed. Heated to 80°C and the reaction time was over 10 hours. After the reaction, the solvent was removed under reduced pressure, and the target product 3b was obtained by column chromatography with a yield of 72%. 1 H NMR (400MHz, CDCl 3 ):δ7.58(d,J=8.0Hz,2H),7.32(d,J=8.0Hz,2H),4.04-4.12(m,1H),3.66-3.74(m,1H),2.41(s, 3H),1.26(t,J=7.1Hz,3H). 13 C NMR (101 MHz, CDCl 3 ): 142.6, 141.7, 129.6, 125.1, 60.7, 21.4, 15.5.

Embodiment 3

[0031] Under nitrogen protection, p-methylphenyltetrafluoroborate diazonium salt 1a (0.2 mmol), DABSO (0.1 mmol), n-butanol 2c (1 mL), cuprous chloride (10 mol%), azobisiso Nitrile (AIBN, 10 mol%) was added to the Schlenk reaction tube and sealed. Heated to 80°C and the reaction time was over 10 hours. After the reaction, the solvent was removed under reduced pressure, and the target product 3c was obtained by column chromatography in a yield of 63%. 1 H NMR (400MHz, CDCl 3 ): δ7.59(d, J=8.0Hz, 2H), 7.33(d, J=8.0Hz, 2H), 3.94-4.00(m, 1H), 3.53-3.59(m, 1H), 2.42(s, 3H), 1.61-1.67(m, 2H), 0.90(t, J=7.4Hz, 3H). 13 C NMR (101MHz, CDCl 3 ): 142.6, 141.8, 129.7, 125.2, 66.1, 23.1, 21.5, 10.3.

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Abstract

The invention relates to the fields of medicine, organic chemical industry and fine chemical industry, in particular to a simple and efficient method for preparing aryl sulfinate compounds. The method is based on aryltetrafluoroborate diazonium salt, bis(sulfur dioxide)-1,4-diazabicyclo[2.2.2]octane adduct (DABSO) and alcohol as raw materials, in copper salt catalyst, oxidant In the presence of nitrogen protection, under the heating reaction conditions of 50-100°C, the aryl sulfinate was synthesized for 10-15 hours. A series of aryl sulfinate compounds can be obtained in high yields after simple post-treatment. Aryltetrafluoroborates with various substituents on the benzene ring, common primary alcohols and secondary alcohols can be used as reaction substrates to obtain corresponding sulfinic acid esters.

Description

technical field [0001] The invention relates to the fields of medicine, organic chemical industry and fine chemical industry, in particular to a copper-catalyzed method for synthesizing a sulfinate compound with sulfur dioxide (DABSO) as a thionyl source and alcohol as a solvent. Background technique [0002] Sulfinates are an important class of compounds that are widely used as intermediates in organic synthesis and as probes for live cell imaging in biochemical assays. Due to the important application value of the research on the synthesis of sulfinate, it has attracted a lot of attention. The traditional synthesis method is obtained by esterification of sulfinyl chloride with alcohol. However, sulfinyl chloride has poor stability, and its synthesis is generally obtained by oxidizing the corresponding thiol or thiophenol, both of which are reagents with low stability and very unpleasant odor. Poor operability. In addition, sodium sulfinate, sulfinic acid, sulfonyl chlor...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C313/04
Inventor 于金涛滕建刚孙松成江
Owner CHANGZHOU UNIV
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