Synthesis method of 1,1-difluoro-2-propylene olefin compound

A synthetic method and technology of propylene hydrocarbons, applied in the preparation of organic compounds, carbon-based compounds, chemical instruments and methods, etc., to achieve the effects of less by-products, high yield, and wide applicability of substrates

Pending Publication Date: 2021-07-27
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Aiming at the shortcomings of the existing synthetic routes, the present invention provides a synthetic method for 1,1-difluoro-2-propene compound, which has the advantages of easy-to-obtain raw materials, simple process, mild conditions, convenient operation, relatively high yield, and Wide range of substances, relatively few by-products, etc.

Method used

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  • Synthesis method of 1,1-difluoro-2-propylene olefin compound
  • Synthesis method of 1,1-difluoro-2-propylene olefin compound
  • Synthesis method of 1,1-difluoro-2-propylene olefin compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]

[0028] To a 25 mL high-pressure nitrogen storage equipped with a magnetic stirrer, add raw materials 1-methyl-4-(3,3,3-trifluoro-1-propynyl)benzene (0.2 mmol), cuprous iodide (0.02 mmol), potassium tert-butyl alkoxide (0.3mmol), B 2 Pin 2(pinacol diboronate) (0.6mmol), tricyclohexylphosphine (PCy3) (0.02mmol), add 2.0mL toluene under argon protection; fix the reaction tube on a magnetic stirrer, and react the mixture at 90°C for 4h Afterwards, the reaction ends; add an appropriate amount of water to the reaction solution, extract with ethyl acetate, dry over anhydrous sodium sulfate, and finally use rotary evaporation to remove the solvent, and the crude product is separated and purified by column chromatography (eluent is petroleum ether) to obtain The target product (2a), yield 60%. The NMR data of this compound are: 1 H NMR (600MHz, CDCl3) δ7.35 (d, J = 7.9Hz, 2H), 7.19 (d, J = 7.9Hz, 2H), 6.87–6.84 (m, 1H), 6.34–6.15 (m, 2H) ,2.38(s,3H). 13 CNMR(151MHz, CD...

Embodiment 2

[0030]

[0031] Substitute 1-methyl-3-(3,3,3-trifluoro-1-propynyl)benzene (1b) for 1-methyl-4-(3,3,3-trifluoro-1-propyne Base) benzene (1a), others are with embodiment 1. Column chromatography (petroleum ether: ethyl acetate = 100:1) gave the target product (2b) in a yield of 67%. The NMR data of this compound are: 1 H NMR (400MHz, CDCl 3 )δ7.30–7.17(m,3H),7.18–7.17(m,1H),6.89–6.83(m,1H),6.40–6.10(m,2H),2.38(s,3H). 13 C NMR (101MHz, CDCl 3 )δ138.61, 137.38(t, J=12.2Hz), 134.52, 130.34, 128.83, 128.05, 124.56, 120.90(t, J=24.0Hz), 115.62(t, J=233.5Hz), 21.45. 19 F NMR (376MHz, CDCl 3 )δ-109.31–-109.50(m,2F).

Embodiment 3

[0033]

[0034] Replace 1-methyl-4-(3,3,3-trifluoro-1-propane) with 1-tert-butyl-4-(3,3,3-trifluoro-1-propynyl)benzene (1c) Alkynyl) benzene (1a), others are the same as in Example 1. Column chromatography (petroleum ether: ethyl acetate = 100:1) gave the target product (2c) in a yield of 70%. The NMR data of this compound are: 1 H NMR (400MHz, CDCl 3 )δ7.42–7.38(m,4H),6.90–6.84(m,1H),6.39–6.10(m,2H),1.34(s,9H). 13 C NMR (101MHz, CDCl 3 )δ152.92, 137.09(t, J=12.3Hz), 131.81, 127.18, 125.90, 120.31(t, J=24.0Hz), 115.76(t, J=233.3Hz), 34.90, 31.35. 19 F NMR (376MHz, CDCl 3 )δ-109.05–-109.23(m,2F).

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Abstract

The invention discloses a synthesis method of a 1,1-difluoro-2-propylene olefin compound. The synthesis method comprises the following steps: with a trifluoromethyl alkyne compound as a raw material, carrying out selective C-F bond activation on trifluoromethyl alkyne in the presence of a catalyst, a ligand, a boron reagent and alkali to obtain the 1,1-difluoro-2-propylene olefin compound with high selectivity. The method has the advantages of environment friendliness, efficiency, mild reaction conditions, convenience in operation, short in reaction time, few in by-products and the like, and is suitable for large-scale production.

Description

technical field [0001] The present invention relates to a method for synthesizing 1,1-difluoro-2-propene compound, which is to synthesize 1,1-difluoro-2-propene by selectively activating the C-F bond of trifluoromethyl alkyne compound The invention relates to an olefin compound, belonging to the field of organic synthesis. Background technique [0002] Fluorinated organic molecules can significantly change the physical, chemical, and biological properties of molecules. Organofluorine compounds have applications in pharmaceuticals, agrochemicals, materials, surfactants, and catalysts. Difluoroalkyl is an important structural unit commonly found in medicines, pesticides and functional materials. Especially in the design and discovery of drugs, it has important applications and significance, and is widely used in drug development. Difluoromethyl (CF 2 H) is hydroxymethyl (CH 2 OH), sulfhydryl (SH) and other groups of bioelectronic isosteres; in addition, as an important fac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C17/00C07C22/08C07C41/18C07C43/225C07C319/20C07C323/09C07C43/29C07C25/24C07C45/61C07C49/80C07C67/30C07C69/78C07D333/54
CPCC07C17/00C07C41/18C07C319/20C07C45/61C07C67/30C07D333/54C07C22/08C07C25/24C07C43/225C07C323/09C07C43/29C07C49/80C07C69/78
Inventor 徐俊刘杨戴建军许华建
Owner HEFEI UNIV OF TECH
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