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A kind of synthetic method of o-aminobenzobenzotrifluoride and derivatives thereof

A technology of o-aminotrifluorotoluene and aminotrifluorotoluene is applied in the field of synthesis of o-aminotrifluorotoluene and derivatives thereof, and can solve the problems such as being unsuitable for industrial mass production, difficulty in synthesizing azide compounds, increasing production costs, and the like, Achieve the effect of convenient production, easy purification, and less waste.

Active Publication Date: 2020-12-08
ZHENGZHOU INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The analysis of the above three synthetic methods shows that the first synthetic method is difficult to synthesize azide compounds and has potential explosion hazards, which greatly limits the application of this method, and this method is not suitable for industrial mass production.
Both the second method and the third method have used noble metal catalysts, which greatly increase the production cost. Although metals such as iron or copper can also realize the synthesis of such compounds, due to a large amount of metal residues and a large amount of solid waste, it is difficult for The purification and environmental protection of compounds brings great pressure
At the same time, nitro or halogenated reaction substrates are also very expensive, which is also a non-negligible reason that limits the application of the above two methods

Method used

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  • A kind of synthetic method of o-aminobenzobenzotrifluoride and derivatives thereof
  • A kind of synthetic method of o-aminobenzobenzotrifluoride and derivatives thereof
  • A kind of synthetic method of o-aminobenzobenzotrifluoride and derivatives thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1-7

[0046] The target compound o-aminobenzotrifluoride has the structural formula:

[0047]

[0048] The reaction equation is:

[0049]

[0050] Synthesized by:

[0051] At room temperature, in a dry 50mL three-necked reaction flask, add a magneton, and then add 20mL of anhydrous acetonitrile, then add the oxidant (1.5mmol) to anhydrous acetonitrile under stirring conditions, and then add trifluoroform Trimethylsilane (213mg, 1.5mmol), then added anhydrous potassium acetate (147mg, 1.5mmol), then heated the reaction solution to 80°C, and dissolved aniline (93mg, 1.0mmol) in 5mL of anhydrous acetonitrile , and then through a constant pressure dropping funnel, slowly add the aniline solution dropwise to the above reaction solution at 80° C. for about 1 hour. After the dropwise addition was completed, the reaction was carried out at 80° C. for 12 hours. The reaction solution was lowered to room temperature, the solid was filtered off, and then the reaction solution was spin-...

Embodiment 8-11

[0059] The target compound o-aminobenzotrifluoride has the structural formula:

[0060]

[0061] The reaction equation is:

[0062]

[0063] Synthesized by:

[0064] At room temperature, in a dry 50mL three-necked reaction flask, add a magnet, and then add 20mL of anhydrous acetonitrile, and then stir the oxidant 1-acetoxy-1,2-phenyliodide-3- (1H)-ketone (460mg, 1.5mmol) was added to anhydrous acetonitrile, then trifluoromethyltrimethylsilane (213mg, 1.5mmol) was added, and alkali (1.5mmol) was added, then the reaction solution was heated to 80 ℃, dissolve aniline (93mg, 1.0mmol) in 5mL of anhydrous acetonitrile, and then slowly add the aniline solution dropwise to the above reaction solution at 80℃ through a constant pressure dropping funnel for about 1 hour. After the dropwise addition was completed, the reaction was carried out at 80° C. for 12 hours. The reaction solution was lowered to room temperature, the solid was filtered off, and then the reaction solution w...

Embodiment 12-15

[0070] The target compound o-aminobenzotrifluoride has the structural formula:

[0071]

[0072] The reaction equation is:

[0073]

[0074] Synthesized by:

[0075] At room temperature, in a dry 50mL three-necked reaction flask, add a magneton, and then add 20mL of solvent, and then stir the oxidant 1-acetoxy-1,2-phenyliodyl-3-(1H )-ketone (460mg, 1.5mmol) was added to the solvent, then trifluoromethyltrimethylsilane (213mg, 1.5mmol) was added, then anhydrous potassium acetate (147mg, 1.5mmol) was added, and the reaction solution was heated to Dissolve aniline (93 mg, 1.0 mmol) in 5 mL of solvent at 80°C, and slowly add the aniline solution dropwise to the above reaction solution at 80°C through a constant pressure dropping funnel for about 1 hour. After the dropwise addition was completed, the reaction was carried out at 80° C. for 12 hours. The reaction solution was lowered to room temperature, the solid was filtered off, and then the reaction solution was spin-dri...

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Abstract

The invention discloses a synthetic method of aminobenzotrifluoride and a derivant thereof. By adopting a method for performing amino-ortho-position trifluoromethylation on an amino-benzene compound,trifluoromethyl trimethylsilane is used a reaction reagent, free radical substitution reaction is carried out on an amino-ortho-position of the amino-benzene compound and then trifluoromethylation isdirectly carried out, so that a target product is obtained. The method disclosed by the invention has the advantages that raw materials are cheap and easy to obtain, the production is convenient, precious metal is not needed, environmental protection and safety are achieved, and purification is easy to carry out; the method can be developed into an industrial production method. Based on that, according to the synthetic method disclosed by the invention, screening and optimization on synthetic conditions of the compound are also carried out, so that the reaction yield is further improved.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a synthesis method of o-aminobenzobenzotrifluoride and derivatives thereof. Background technique [0002] O-aminotrifluorotoluene and its derivatives are an important class of organic molecular skeletons, which widely exist in chemical raw materials and pharmaceutical active molecules. [0003] The synthesis method of this type of compound mainly contains following several kinds at present: [0004] (1) With o-trifluoromethyl azide benzene compound as raw material, under palladium catalysis, adopt sodium borohydride to make hydrogen source, and reduction obtains target product, and reaction formula is as follows (New Journal of Chemistry, 40 (11), 9550 -9555;2016): [0005] [0006] (2) Using o-trifluoromethylnitrobenzene compounds as raw materials, catalytic hydrogenation on palladium carbon or reduction with iron powder to obtain the target product, the reaction ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/68C07C211/52C07C253/30C07C255/58C07C227/16C07C229/60C07C315/04C07C317/36
CPCC07C209/68C07C227/16C07C253/30C07C315/04C07C211/52C07C255/58C07C229/60C07C317/36
Inventor 李华王焕锋姜巧娟
Owner ZHENGZHOU INST OF TECH
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