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Synthetic method of aryl sulfide type compound

A synthetic method and technology of aryl sulfide, applied in the formation/introduction of mercapto/thioether groups, chemical instruments and methods, thioether preparation, etc., can solve problems such as poor controllability, serious environmental pollution, and low compatibility , to achieve the effects of mild reaction conditions, simple reaction operation, and simple raw materials

Active Publication Date: 2015-06-24
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Due to the strong coordination and complexation effect of the lone pair of electrons on the sulfur atom, the metal is poisoned and the catalytic cycle efficiency of the metal is greatly reduced; the controllability is poor, and the free radical initiation and conversion process is difficult to control; the compatibility is low, and the lack of systemic high compatibility vulcanization
In addition, production and manufacturing are also facing difficulties: foul smell in the process, serious environmental pollution; unstable reagents, easy to oxidize; difficult to obtain raw materials, high cost, etc. These problems restrict the development of the vulcanization industry

Method used

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  • Synthetic method of aryl sulfide type compound
  • Synthetic method of aryl sulfide type compound
  • Synthetic method of aryl sulfide type compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Synthesis of phenyl (4-methylphenyl) sulfide:

[0025]

[0026] Under nitrogen atmosphere, add substrate 1a (0.1mmol, 22.6mg), 2a (0.15mmol, 18.3mg), Cu(OTf) in a 25mL test tube reactor 2 (0.02mmol, 7.2mg), 1,10-phenanthroline (0.04mmol, 7.2mg), Ag 2 CO 3 (0.12mmol, 33.1mg), K 3 PO 4 (0.14mmol, 29.7mg), DTBP (0.1mmol, 18.5μL), CF 3 SO 3 H (3.0 μL), and DMF (2.0 mL). The reaction system was heated to 80°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 3a (40%). R f =0.80 (petroleum ether); 1 H NMR (400MHz, CDCl3): δ7.18-7.24(m, 6H), 7.11-7.13(m, 1H), 7.06(d, J=8.0Hz, 2H), 2.27(s, 3H); 13C NMR (400MHz, CDCl3): δ137.6, 137.1, 132.3, 131.3, 130.0, 129.8, 129.0, 126.4, 21.1; IR (neat) 2950, ​​2851, 1896, 1492, 1477, 808, 739, 690cm -1 ; HRMS (EI) cal...

Embodiment 2

[0028] Synthesis of phenyl (4-methylphenyl) sulfide:

[0029]

[0030] Under carbon dioxide atmosphere, add substrate 1a (0.1mmol, 22.6mg), 2a (0.15mmol, 18.3mg), Cu(OTf) into a 25mL test tube reactor 2 (0.02mmol, 7.2mg), 1,10-phenanthroline (0.04mmol, 7.2mg), Ag 2 CO 3 (0.12mmol, 33.1mg), K 3 PO 4 (0.14mmol, 29.7mg), DTBP (0.1mmol, 18.5μL), CF 3 SO 3 H (3.0 μL), and DMF (2.0 mL). The reaction system was heated to 80°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 3a (85%). The product data is the same as Example 1.

Embodiment 3

[0032] Synthesis of phenyl (4-methylphenyl) sulfide:

[0033]

[0034] Under carbon dioxide atmosphere, add substrate 1a (0.1mmol, 22.6mg), 2a (0.15mmol, 18.3mg), Cu(OTf) into a 25mL test tube reactor 2 (0.02mmol, 7.2mg), 1,10-phenanthroline (0.04mmol, 7.2mg), Ag 2 CO 3 (0.12mmol, 33.1mg), K 3 PO 4 (0.14 mmol, 29.7 mg), DTBP (0.1 mmol, 18.5 μL), and DMF (2.0 mL). The reaction system was heated to 80°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 3a (67%). The product data is the same as Example 1.

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PUM

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Abstract

The invention discloses a synthetic method of an aryl sulfide type compound shown by a formula (3). In a reaction solvent, an aryl or alkenyl thiosulfate type derivative and a boric acid, boric acid grease or borate type derivative are used as reaction raw materials and react with each other to obtain a polysubstituted aryl sulfide type compound under the action of a metal copper catalyst. According to the synthetic method disclosed by the invention, reaction conditions are mild, raw materials are easily-available and low in price, the reaction operation is simple, the yield is relatively high, and a key skeleton structure is provided for the synthesis of many natural products and medicaments, so that the method can be widely applicable to industrial scale production. A formula is shown in the specification.

Description

technical field [0001] The invention specifically relates to a synthesis method for preparing aryl sulfide compounds, which belongs to the technical field of organic compound technology application. Background technique [0002] Sulfur-containing compounds are closely related to the national economy and the people's livelihood, and play an important role in the process of human survival and development. It widely exists in life molecules, optoelectronic materials, natural products, medicines and foods. For example: the iron-sulfur protein that transports oxygen, the disulfide bridge that shapes the secondary structure of DNA and RNA proteins, and the sulfur atoms in the star molecules of drugs such as penicillin and esomeprazole, all play a vital role . The special odor of foods such as garlic, onion, and durian that we eat daily is also caused by sulfides, but it is precisely because of these substances that they have the functions of sterilization, anti-inflammatory, and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B45/06C07C319/14C07C321/30C07C323/62C07C323/20C07C323/09C07F17/02C07D333/34C07D307/82C07D213/70C07D215/36C07D311/72C07D333/76C07D317/56
Inventor 姜雪峰乔宗君
Owner EAST CHINA NORMAL UNIV
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