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Method for synthesizing 2-bromo-1,1,2,2-tetrafluoroethyl substituted aryl building block

The technology of a tetrafluoroethyl group and a synthesis method is applied in the field of synthesis of aryl building blocks, and achieves the effects of short reaction steps, simple and easy-to-obtain raw materials and reagents, and green sources.

Active Publication Date: 2017-12-08
ZUNYI MEDICAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The present invention intends to provide a method for synthesizing 2-bromo-1,1,2,2-tetrafluoroethyl substituted aryl building blocks, so as to solve the defect that such compounds cannot be efficiently and concisely synthesized in the prior art

Method used

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  • Method for synthesizing 2-bromo-1,1,2,2-tetrafluoroethyl substituted aryl building block
  • Method for synthesizing 2-bromo-1,1,2,2-tetrafluoroethyl substituted aryl building block
  • Method for synthesizing 2-bromo-1,1,2,2-tetrafluoroethyl substituted aryl building block

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preparation example Construction

[0033] The invention provides a method for synthesizing dibromotetrafluoroethane-substituted aniline and its derivatives. Preferably, the method includes the step of: in an organic solvent, at a certain temperature (such as 0°C-80°C; preferably 10°C-50°C), under the irradiation of blue light or green light in visible light, to contain iridium , the complex of ruthenium is a photocatalyst, and the compound of formula A (i.e. aniline or its derivatives) is reacted with the compound of formula B) for a period of time (such as 1 to 40 hours) to form the compound of formula C (dibromotetrafluoroethane substituted Aniline and derivatives thereof), and D compounds can be obtained through some classic organic reactions;

[0034]

[0035] In various forms, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 Defined as above.

[0036] More preferably, the compound of formula A is a compound selected from the group consisting of:

[0037]

[0038] Compounds of formula A and formula B of the ...

Embodiment 1

[0050]

[0051] To a 25mL reaction tube, add 1.3mg (0.5mol%) Ir(PPy), Na 2 CO 3 (0.4mmol), compound A-1 (102mmol, 3 equivalents), after argon replacement three times, add 2mL of acetonitrile (MeCN), inject 50μL (0.40mmol) of compound B-1, and stir for 24 hours under blue light irradiation to obtain compound C-1, 78% yield. 1 HNMR (400MHz, CDCl 3 )δ7.13(1H), 7.10(d, J=8.4Hz, 1H), 6.62(d, J=8.4Hz, 1H), 3.81(br, 2H), 2.26(s, 3H). 19 FNMR (376MHz, CDCl 3 ) δ - 64.5 (t, J = 5.6Hz, 2F), -105.4 (t, J = 5.6Hz, 2F).

Embodiment 2

[0053]

[0054] Into a 25mL reaction tube, add 1.3mg (0.5mol%) Ir(PPy) 3 , K 3 PO 4 (0.4mmol), compound A-1 (1.2mmol, 3 equivalents), nitrogen replacement three times, adding 2mL of acetonitrile (MeCN), injecting 50μL (0.40mmol) of compound B-1, and stirring for 24 hours under blue light irradiation, to obtain compound C-1, 65% yield. 1 HNMR (400MHz, CDCl 3 )δ7.13(1H), 7.10(d, J=8.4Hz, 1H), 6.62(d, J=8.4Hz, 1H), 3.81(br, 2H), 2.26(s, 3H). 19 FNMR (376MHz, CDCl 3 ) δ - 64.5 (t, J = 5.6Hz, 2F), -105.4 (t, J = 5.6Hz, 2F).

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Abstract

The invention discloses a method for synthesizing a 2-bromo-1,1,2,2-tetrafluoroethyl substituted aryl building block under simple conditions. The method comprises the following steps: based on aniline and 1,2-dibromotetrafluoroethane compounds, by taking a complex taking iridium, ruthenium and other transition metals as a core as a catalyst, preparing various aniline structures substituted by bromotetrafluoroethane at high efficiency, and further performing derivatization on amino, thereby obtaining multiple 2-bromo-1,1,2,2-tetrafluoroethyl aromatic hydrocarbon compounds. The method takes cheap and readily available aniline and derivatives thereof and the dibromotetrafluoroethane as raw materials, and has the advantages of being small in catalyst amount, wide in substrate application range, easy and convenient to operate, high in reaction efficiency and the like, and after the reaction is ended, another bromine atom is well remained. Meanwhile, the products can be easily converted into 1,1,2,2-tetrafluoroethyl bridged compounds, and have very wide and important purposes in the fields of pesticides, liquid crystal materials, molecular imaging and the like.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing 2-bromo-1,1,2,2-tetrafluoroethyl-substituted aryl building blocks. Background technique [0002] The development of fluoroalkylation reactions has attracted extensive attention due to the ability of the introduced fluoroalkyl group to modify the chemical, physical, and biological activities of organic compounds. Tetrafluoroethyl is an important class of fluoroalkyl groups, and the tetrafluoroethylene bridge (-CF2CF2-) has many applications in materials and agrochemical research. Typically, the ArCF2CF2Ar structure is prepared by fluorination methods, such as fluorine addition to arylacetylenes or deoxyfluorination of 1,2-dicarbonyl compounds. More recently, Gouverneur, Togni, Beier and Hu used the fluoroalkylation method. In these reactions, aryl CF2CF2Br, aryl CF2CF2SiMe3 and hypervalent iodine reagents were used as fluoroalkylating reagent...

Claims

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Application Information

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IPC IPC(8): C07C22/08C07C17/263C07C209/68C07C211/52C07C213/08C07C217/84C07C319/20C07C323/36C07C231/12C07C233/25C07C233/15C07D215/12C07F7/08C07J1/00
CPCC07C17/263C07C22/08C07C209/68C07C211/52C07C213/08C07C217/84C07C231/12C07C233/15C07C233/25C07C319/20C07C323/36C07D215/12C07F7/081C07J1/0081
Inventor 贺春阳李晓飞孔晶晶黄洋
Owner ZUNYI MEDICAL UNIVERSITY
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