Unlock instant, AI-driven research and patent intelligence for your innovation.

A kind of synthetic method of aryl sulfide compound

A technology of aryl sulfide and synthesis method, which is applied in the field of synthesis of aryl sulfide compounds, can solve the problems of insufficient substrate adaptability, serious pollution, easy oxidation, etc., and achieves low cost and simple reaction operation , the effect of less pollution

Active Publication Date: 2016-08-17
EAST CHINA NORMAL UNIV
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in this method, mercaptans and thiophenols need to be prepared in advance, and the adaptability of the substrate is not wide enough. Not only the taste is strong, the pollution is serious, and it is easy to be oxidized, so the application of this method is restricted.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of synthetic method of aryl sulfide compound
  • A kind of synthetic method of aryl sulfide compound
  • A kind of synthetic method of aryl sulfide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Synthesis of n-butyl (4-acetylphenyl) sulfide:

[0025]

[0026] Under nitrogen atmosphere, add substrate 2bm (0.2mmol, 49.2mg), 1-chlorobutane (3.0mmol, 276.0mg), PdCl 2 (dppf) (0.02mmol, 14.6mg), dppf (0.01mmol, 5.6mg), Cs 2 CO 3 (0.3mmol, 195.0mg), Na 2 S 2 o 3 5H 2 O (0.5mmol, 248.0mg), CH 3 CN(4.0mL) and H 2 O (0.2 mL), the reaction system was heated to 150°C for reaction. After the reaction was detected by TLC, the system was cooled to room temperature. The reaction was quenched with saturated aqueous ammonium chloride, extracted with ethyl acetate (3*10 mL), and purified by column chromatography to obtain product 2b (45%). R f =0.35 (ethyl acetate: petroleum ether=50:1); 1 H NMR (400MHz, CDCl 3 ): δ7.77(d, J=8.4Hz, 2H), 7.21(d, J=8.4Hz, 2H), 2.91(t, J=7.2Hz, 2H), 2.48(s, 3H), 1.64-1.57 (m, 2H), 1.45-1.36(m, 2H), 0.87(t, J=7.2Hz, 3H); 13 C NMR (100MHz, CDCl 3 ): δ197.1, 144.9, 133.6, 128.6, 126.1, 31.5, 30.7, 26.3, 21.9, 13.5; -1 ; HRMS (EI) cal...

Embodiment 2

[0028] Synthesis of n-butyl (4-acetylphenyl) sulfide:

[0029]

[0030] Under nitrogen atmosphere, add substrate 2bm (0.2mmol, 49.2mg), 1-chlorobutane (3.0mmol, 276.0mg), Pd(dba) into a sealed tube of 25mL 2 (0.02mmol, 11.5mg), dppp (0.03mmol, 12.2mg), Cs 2 CO 3 (0.3mmol, 195.0mg), Na 2 S 2 o 3 5H 2 O (0.5mmol, 248.0mg), CH 3 CN(4.0mL) and H 2 O (0.2 mL). The reaction system was heated to 150°C for reaction. After the reaction was detected by TLC, the system was cooled to room temperature. The reaction was quenched with saturated aqueous ammonium chloride, extracted with ethyl acetate (3*10 mL), and purified by column chromatography to obtain product 2b (22%). The product analysis data is the same as Example 1.

Embodiment 3

[0032] Synthesis of n-butyl (4-acetylphenyl) sulfide:

[0033]

[0034] Under nitrogen atmosphere, add substrate 2bm (0.2mmol, 49.2mg), 1-chlorobutane (3.0mmol, 276.0mg), PdCl 2 (dppf) (0.02mmol, 14.6mg), Cs 2 CO 3 (0.3mmol, 195.0mg), Na 2 S 2 o 3 5H 2 O (0.5mmol, 248.0mg), CH 3 CN(4.0mL) and H 2 O (0.2 mL). The reaction system was heated to 150°C for reaction. After the reaction was detected by TLC, the system was cooled to room temperature. The reaction was quenched with saturated aqueous ammonium chloride, extracted with ethyl acetate (3*10 mL), and purified by column chromatography to obtain product 2b (35%). The product analysis data is the same as Example 1.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a synthetic method of an aryl thioether compound as shown in a formula (3). The polysubstituted aryl thioether compound is obtained by using aryl iodide or an aryl trifluoromethane sulphonate derivative and halogenated hydrocarbon as reaction raw materials and Na2S2O3 as a vulcanization reagent and reacting in a reaction solvent under the effect of a metal palladium catalyst. The synthetic method is mild in reaction conditions, simple in reaction operation and relatively high in productivity, can provide key skeleton structures for synthesis of lots of natural products and medicines and can be widely applied to industrialization scale production.

Description

technical field [0001] The invention belongs to the technical field of organic compound technology application, and in particular relates to a synthesis method for preparing aryl sulfide compounds. Background technique [0002] Aryl sulfide compounds (that is, organic compounds containing C-S bonds in the molecule) are a very important class of compounds, which widely exist in various medicinal chemistry (as shown below), material chemistry and food chemistry. Therefore, from some structures It is particularly important to construct C-S bonds on compounds that are simple and commercially available in large quantities. [0003] [0004] The traditional method of synthesizing aryl sulfide compounds is mainly through the preparation of thiol or thiophenol compounds. However, in this method, mercaptans and thiophenols need to be prepared in advance, and the adaptability of the substrate is not wide enough. Not only the taste is strong, the pollution is serious, and it is eas...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/22C07C319/14C07C323/62C07C323/09C07D307/10C07D213/70C07D405/12C07F7/18C07D307/64C07D333/34C07D333/38C07D241/18C07D401/12C07D307/82C07D333/62C07D277/74C07D263/58C07D261/16
Inventor 姜雪峰乔宗君
Owner EAST CHINA NORMAL UNIV