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Synthesis method of aromatic vinyl trifluoromethylthio ether compound

A technique for the synthesis of aromatic vinyl trifluoromethyl sulfide, which is applied in the fields of sulfide preparation, organic chemistry, etc., can solve the problems of low substrate universality, long reaction time, high reaction temperature, etc., and achieve good industrial application Foreground, high substrate universality, good catalytic effect

Active Publication Date: 2019-02-15
万博新材料科技(南通)有限公司
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Problems solved by technology

Among the reported synthetic methods about arylvinyl trifluoromethyl sulfide compounds: (1) the target product is synthesized by decarboxylation of cinnamic acid compounds, and this method uses 2 times the equivalent of CuSO 4 ·5H 2 O is as catalyzer, and the utilization ratio of copper salt catalyst is very low, secondly, the yield of this reaction is on the middle, and a part of raw material has not been realized effective transformation; iodide and bromide) with CuSCF 3 and (bpy)CuSCF 3 Reaction to synthesize the target product, the reaction conditions of this method are relatively harsh, the reaction temperature is higher, respectively 110 ° C and 100 ° C, and the reaction time is relatively long. In addition, the copper trifluoromethylsulfide reagent used is unstable and the price is more expensive. Expensive; (3) When using aryl boronic acid, styrene or phenylacetylene reaction substrates to synthesize target products, the substrate universality is not high

Method used

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  • Synthesis method of aromatic vinyl trifluoromethylthio ether compound
  • Synthesis method of aromatic vinyl trifluoromethylthio ether compound
  • Synthesis method of aromatic vinyl trifluoromethylthio ether compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Synthesis of trans-4-methylstyryl trifluoromethyl sulfide

[0028] Weigh 0.082g of trans-4-methylnitrostyrene, 0.125g of silver trifluoromethylsulfide, 0.014g of copper trifluoroacetate, 0.174g of dipotassium hydrogen phosphate and 0.228g of ammonium persulfate, and add them in turn with a magnetic stirring bar Add 5.0 mL of dimethyl sulfoxide to a 50 mL reaction tube, and place it under a nitrogen atmosphere at 60° C. for 4-6 hours.

[0029] After the reaction, the reaction solution was filtered, washed, dried and separated and purified in sequence to obtain 0.093 g of a colorless oily liquid with a yield of 85%. 1 H NMR (400MHz, CDCl 3 )δ7.32(d, J=8.1Hz, 2H), 7.20(d, J=8.0Hz, 2H), 7.02(d, J=15.3Hz, 1H), 6.70(d, J=15.3Hz, 1H) ,2.39(s,4H); 19 F NMR (376MHz, CDCl 3 )δ-42.91(s,3F); 13 C NMR (101MHz, CDCl 3 )δ141.76(d, J=0.7Hz), 139.4(s), 132.4(s), 129.7(q, J=307.9Hz), 129.6(s), 126.8(s), 110.3(q, J=3.0 Hz), 21.3(s).

Embodiment 2

[0030] Example 2: Synthesis of trans-4-tert-butyl styryl trifluoromethyl sulfide

[0031] Weigh 0.103g of trans-4-tert-butylnitrostyrene, 0.125g of silver trifluoromethylsulfide, 0.014g of copper trifluoroacetate, 0.174g of dipotassium hydrogen phosphate and 0.228g of ammonium persulfate, and add them in sequence Add 5.0 mL of dimethyl sulfoxide to a 50 mL reaction tube, and place it under a nitrogen atmosphere at 60° C. for 4-6 hours.

[0032] After the reaction, the reaction solution was filtered, washed, dried, separated and purified in sequence to obtain 0.107 g of a colorless oily liquid with a yield of 82%. 1 H NMR (400MHz, CDCl 3 )δ7.45(d, J=8.5Hz, 2H), 7.40(d, J=8.5Hz, 2H), 7.06(d, J=15.3Hz, 1H), 6.75(d, J=15.2Hz, 1H) ,1.38(s,9H); 19 F NMR (376MHz, CDCl 3 )δ-42.91(s,3F); 13 C NMR (101MHz, CDCl 3 )δ152.7(s), 141.8(d, J=0.8Hz), 132.4(s), 129.7(q, J=307.9Hz), 126.7(s), 125.8(s), 110.5(q, J=3.0 Hz), 34.8(s), 31.2(s).

Embodiment 3

[0033] Example 3: Synthesis of trans-4-chlorostyryl trifluoromethyl sulfide

[0034] Weigh 0.092g of trans-4-chloronitrostyrene, 0.125g of silver trifluoromethylsulfide, 0.014g of copper trifluoroacetate, 0.174g of dipotassium hydrogen phosphate and 0.228g of ammonium persulfate, and add in sequence Add 5.0 mL dimethyl sulfoxide to a 50 mL reaction tube, and place it under a nitrogen atmosphere at 60° C. for 4-8 hours.

[0035] After the reaction, the reaction solution was filtered, washed, dried, separated and purified in sequence to obtain 0.086 g of a colorless oily liquid with a yield of 72%. 1 H NMR (400MHz, CDCl 3 )δ7.35(s, 4H), 6.97(d, J=15.4Hz, 1H), 6.75(d, J=15.4Hz, 1H);19 F NMR (376MHz, CDCl 3 )δ-42.62(s,3F); 13 C NMR (101MHz, CDCl 3 )δ139.3(d, J=0.7Hz), 135.0(s), 133.6(s), 129.6(q, J=308.0Hz), 129.1(s), 127.97(s), 112.7(dd, J=6.3 ,3.1Hz). Comparative example 1:

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Abstract

The invention discloses a synthesis method of an aromatic vinyl trifluoromethylthio ether compound, and belongs to the technical field of chemical synthesis. According to the synthesis method disclosed by the invention, the aromatic vinyl trifluoromethylthio ether compound is prepared by taking trans-nitro aryl ethylene as a substrate, silver trifluoromethylthio as a thioether reagent and copper trifluoroacetic acid as a catalyst, and adding an oxidizing agent and an additive. Raw materials used by the method are easy to obtain, the reaction is simple to operate, the yield is high, and the substrate universality is good; the obtained aromatic vinyl trifluoromethylthio ether product has important application in the medicine, pesticide and function material fields.

Description

technical field [0001] The invention relates to a method for synthesizing aromatic vinyl trifluoromethyl sulfide compounds, belonging to the technical field of chemical synthesis. Background technique [0002] At present, the trifluoromethyl sulfide reaction is a research hotspot in the field of organic chemistry. More and more researchers at home and abroad have begun to pay attention to the trifluoromethyl sulfide reaction. The main reason is the unique physical and chemical properties of trifluoromethylthio and the important Application prospect. For example, the trifluoromethylthio group has a strong electron-withdrawing ability, which can effectively reduce the electron cloud density of the substrate and greatly improve the metabolic stability of the molecule; in addition, the sulfur atom can be further oxidized into sulfoxide and sulfone functional groups , so that the activity of the product substrate can be flexibly regulated according to the needs. At the same tim...

Claims

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Application Information

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IPC IPC(8): C07C319/14C07C323/03C07C323/07
CPCC07C319/14C07C323/03C07C323/07
Inventor 郑昌戈刘洋洪建权
Owner 万博新材料科技(南通)有限公司
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