Method for preparing diaryl disulfide and diaryl diselenide under catalysis of aqueous phase

A technology for catalysts to catalyze sulfur and catalysts, applied in chemical instruments and methods, formation/introduction of mercapto/sulfide groups, organic chemical methods, etc., can solve problems such as cumbersome preparation process, high cost, and reduced reaction yield

Inactive Publication Date: 2011-04-13
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above methods all use organic solvents to varying degrees, the preparation process is cumbersome, the cost is relatively high, and the reaction yield is often reduced due to the occurrence of side reactions.
[0003] The preparation of disulfide and diselenide compounds by catalyzing halogenated aromatic hydrocarbons in pure aqueous systems has rarely been reported so far

Method used

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  • Method for preparing diaryl disulfide and diaryl diselenide under catalysis of aqueous phase
  • Method for preparing diaryl disulfide and diaryl diselenide under catalysis of aqueous phase
  • Method for preparing diaryl disulfide and diaryl diselenide under catalysis of aqueous phase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Preparation of diphenyl disulfide from iodobenzene: Add 1 mmol of iodobenzene, 0.05 mmol of copper complex, 1 mmol of sodium hydroxide, 3.0 mmol of sulfur powder, 0.1 mmol of tetrabutylammonium fluoride, and 2 mL of water into a reaction vessel . React in an oil bath at 100°C for 30 hours and cool to room temperature. The product was extracted with ethyl acetate, concentrated under reduced pressure, and purified by column chromatography to obtain a light yellow oily product with a yield of 95%.

Embodiment 2

[0027] Example 2: Preparation of p-methylphenylbenzene disulfide by p-methyliodobenzene: add 0.5mmol of iodobenzene, 0.5mmol of p-methyliodobenzene, 0.05mmol of copper complex, 1mmol of sodium hydroxide, sulfur powder 3.0mmol, tetrabutylammonium fluoride 0.1mmol, water 2mL. React in an oil bath at 100°C for 30 hours and cool to room temperature. The product was extracted with ethyl acetate and concentrated under reduced pressure. The product was purified by column chromatography to obtain a light yellow liquid with a yield of 93%.

Embodiment 3

[0028] Embodiment 3: p-methoxyphenylbenzene disulfide is prepared from p-methoxy iodobenzene: the preparation method is the same as in Example 2, adding 0.5 mmol of iodobenzene and 0.5 mmol of p-methoxy iodobenzene to obtain a colorless liquid, producing The rate is 93%.

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PUM

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Abstract

The invention discloses a method for preparing diaryl disulfide and diaryl diselenide under the catalysis of an aqueous phase. A water-soluble catalyst is used for efficiently catalyzing the reaction of sulfur powder or selenium powder with aryl halide in the pure aqueous phase, so the method for preparing disulfide-bond-containing and diselenide-bond-containing aromatic compounds is environmentally-friendly, simple and convenient to operate, safe, low in cost and efficient. Compared with the prior art, the method can be suitable for a large number of functional groups, ensures high yield and few side products, and is simple and convenient to operate, safe, low in cost and environmentally-friendly.

Description

1. Technical field [0001] The invention relates to a method for preparing a diaryl disulfide compound and a diaryl diselenide compound by using sulfur powder and selenium powder respectively as a vulcanizing agent and a selenizing agent in an aqueous phase to catalyze a halogenated aromatic hydrocarbon. 2. Background technology [0002] Diaryl disulfide compounds and diaryl diselenide compounds not only have very important industrial application value, such as being widely used in the production of free radical polymerization initiators and polymerization regulators of unsaturated polyesters and other free radical generators, but also It is also an important organic synthesis intermediate, which is used in the synthesis and production of drugs. The synthetic method of disulfide compound and diselenide compound is always the focus of research (referring to: (a) CN200480037765; (b) CN99102761.2; (c) M.Lácová, R. P. A. Bohác, H.M. El-Shaaer, Tetrahedron 2010, 66, 1410.). A...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B45/06C07B47/00C07C319/24C07C321/28C07C323/20C07C323/09C07C391/02
Inventor 周向葛柯方屈延阳邓杭
Owner SICHUAN UNIV
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