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Preparation method of alcohol compound containing fluorine atoms

A compound, fluorine atom technology, applied in the field of preparation of alcohol compounds, achieves the effects of wide source of raw materials, simple feeding method and mild reaction conditions

Pending Publication Date: 2020-12-08
CHUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although alcohol compounds containing fluorine atoms are extremely important in organic chemistry and medicinal chemistry, the direct preparation of alcohol compounds containing fluorine atoms has not been reported, so high yield, high functional group compatibility, and easy operation The preparation of alcohol compounds containing fluorine atoms has very important application value

Method used

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  • Preparation method of alcohol compound containing fluorine atoms
  • Preparation method of alcohol compound containing fluorine atoms
  • Preparation method of alcohol compound containing fluorine atoms

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1, the reaction formula of this embodiment is as follows:

[0037]

[0038] (1) Under air, nickel(II) diethylene glycol dimethyl ether complex (10mol%), 4,4'-di-tert-butyl-2,2'-bipyridine (12mol%), zinc Powder (3eq), sodium iodide (0.5eq), and triethylamine hydrochloride (1.2eq) were added to a sealed reaction tube with a branch tube containing magnetons, and the reaction tube was pumped three times with argon. Under argon protection, add N,N-dimethylacetamide to the reaction tube, stir at room temperature for 5 minutes, then add substrate 1a and substrate 2a to the reaction solution in turn under argon protection, and stopper The piston was placed in a 30°C oil bath and stirred for 10 hours.

[0039] (2) Add ethyl acetate to the material obtained in step (1) and mix thoroughly, filter out the solid residue with a short silica gel column, and keep the organic phase.

[0040] (3) Spin dry the solvent in the organic phase obtained in step (2) to obtain a c...

Embodiment 2

[0042] The reaction formula of this embodiment is as follows:

[0043]

[0044] (1) Under air, nickel(II) diethylene glycol dimethyl ether complex (10mol%), 4,4'-di-tert-butyl-2,2'-bipyridine (12mol%), zinc Powder (3eq), sodium iodide (0.5eq), and triethylamine hydrochloride (1.2eq) were added to a sealed reaction tube with a branch tube containing magnetons, and the reaction tube was pumped three times with argon. Under argon protection, add N,N-dimethylacetamide to the reaction tube, stir at room temperature for 5 minutes, then add substrate 1b and substrate 2a to the reaction solution in sequence under argon protection, and stopper The piston was placed in a 30°C oil bath and stirred for 10 hours.

[0045] (2) Add ethyl acetate to the material obtained in step (1) and mix thoroughly, filter out the solid residue with a short silica gel column, and keep the organic phase.

[0046] (3) Spin dry the solvent in the organic phase obtained in step (2) to obtain a crude produ...

Embodiment 3

[0048] The reaction formula of this embodiment is as follows:

[0049]

[0050] (1) Under air, nickel(II) diethylene glycol dimethyl ether complex (10mol%), 4,4'-di-tert-butyl-2,2'-bipyridine (12mol%), zinc Powder (3eq), sodium iodide (0.5eq), and triethylamine hydrochloride (1.2eq) were added to a sealed reaction tube with a branch tube containing magnetons, and the reaction tube was pumped three times with argon. Under argon protection, add N,N-dimethylacetamide to the reaction tube, stir at room temperature for 5 minutes, then add substrate 1c and substrate 2c to the reaction solution in sequence under argon protection, and stopper The piston was placed in a 30°C oil bath and stirred for 10 hours.

[0051] (2) Add ethyl acetate to the material obtained in step (1) and mix thoroughly, filter out the solid residue with a short silica gel column, and keep the organic phase.

[0052] (3) Spin dry the solvent in the organic phase obtained in step (2) to obtain a crude produ...

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Abstract

The invention discloses a preparation method of an alcohol compound containing fluorine atoms, which comprises the following steps: taking halogenated alkane and trifluoro-alkene as raw materials, reacting in a solvent under the actions of a nickel catalyst, a ligand and zinc powder according to the following reaction formula to prepare the alcohol compound containing fluorine atoms. The fluorineatom-containing alcohol compound prepared by the method is high in yield and mild in reaction condition. According to the method disclosed by the invention, synthesis of the fluorine atom-containing alcohol compound is realized for the first time. Meanwhile, the reaction system is simple in feeding mode, and reagents sensitive to moisture and air do not need to be used. The halogenated alkane compound can be directly synthesized from an alcohol compound, and the reaction functional group is excellent in compatibility and high in reaction yield.

Description

technical field [0001] The invention relates to the technical field of compound substance preparation, in particular to a method for preparing alcohol compounds containing fluorine atoms. Background technique [0002] Fluorine-containing compounds are an important class of structural fragments. The introduction of fluorine atoms into compounds can significantly improve the metabolic stability, lipophilicity and bioavailability of parent molecules. Therefore, fluorine-containing compounds have been widely used in pharmaceuticals, agrochemicals, materials, and life sciences. In addition, alcohol compounds are also important organic structural fragments, which widely exist in various active molecules and drug molecules. At the same time, alcohol compounds are also important organic synthesis intermediates. The figure below shows some important fluorochemicals. [0003] [0004] Although alcohol compounds containing fluorine atoms are extremely important in organic chemist...

Claims

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Application Information

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IPC IPC(8): C07C29/36C07C33/48C07D317/54C07C41/30C07C43/225C07D209/26C07J1/00
CPCC07C29/36C07D317/54C07C41/30C07D209/26C07J1/0059C07C33/486C07C43/225
Inventor 陆晓雨王晴晴李佳美
Owner CHUZHOU UNIV
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