Aromatic ring or heteroaromatic trifluoromethyl ketone compound and preparation method thereof

A technology of trifluoromethyl ketone and trifluoromethyl trimethylsilicon, which is applied in the field of organic synthesis, can solve the problems of complex post-processing, low yield, large oxidant equivalent, etc., and achieves easy purification, high yield, and oxidant. small equivalent effect

Inactive Publication Date: 2013-07-24
TETRANOV PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The trifluoromethyl ketone compound currently on the market cannot meet the actual needs, and its preparation method is mainly obtained by oxidation of oxidants such as manganese dioxide and potassium permanganate
These methods have disadvantages such as complex post-treatment, low yield, and large equivalent of oxidant

Method used

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  • Aromatic ring or heteroaromatic trifluoromethyl ketone compound and preparation method thereof
  • Aromatic ring or heteroaromatic trifluoromethyl ketone compound and preparation method thereof
  • Aromatic ring or heteroaromatic trifluoromethyl ketone compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The aromatic ring or aromatic heterocyclic trifluoromethyl ketone compound in this embodiment is trifluoroacetophenone, and its structural formula is:

[0029]

[0030] The preparation method of the trifluoroacetophenone of the present embodiment may further comprise the steps:

[0031] 1) Add benzaldehyde, K 2 CO 3 Dissolve in DMF according to the molar ratio of 20:1, and put it into a three-neck glass bottle together with the magnet, and repeatedly vacuumize and flush it into N 2 After 4 times, place the three-neck glass bottle in an ice bath and stir vigorously; the amount of DMF is to add 3L of DMF per mole of benzaldehyde;

[0032] 2) When the temperature in step 1) drops to 0°C, slowly add trifluoromethyl trimethyl silicon dropwise according to the benzaldehyde:trifluoromethyl trimethyl silicon molar ratio of 1:1; After 30 min of fluoromethyl ketone, the temperature was raised to room temperature for 0.5 h of reaction;

[0033] 3) Slowly add 5 mL of 4M HCl ...

Embodiment 2

[0039] The aromatic ring or aromatic heterocyclic trifluoromethyl ketone compound in this embodiment is p-methyl trifluoroacetophenone, and its structural formula is:

[0040]

[0041] The preparation method of the p-methyltrifluoroacetophenone of the present embodiment comprises the following steps:

[0042] 1) P-tolualdehyde, K 2 CO 3 Dissolve in DMF according to the molar ratio of 20:1, and put it into a three-neck glass bottle together with the magnet, and repeatedly vacuumize and flush it into N 2 After 4 times, the three-neck glass bottle was placed in an ice bath and stirred vigorously; the amount of DMF was 4L of DMF per mole of p-tolualdehyde;

[0043] 2) When the temperature in step 1) drops to -5°C, slowly add trifluoromethyl trimethyl silicon dropwise according to the molar ratio of p-tolualdehyde: trifluoromethyl trimethyl silicon; After dropping the trifluoromethyl ketone for 15 minutes, the temperature was raised to room temperature for 48 hours;

[0044]...

Embodiment 3

[0050] The aromatic ring or aromatic heterocyclic trifluoromethyl ketone compound in this embodiment is p-methoxy trifluoroacetophenone, and its structural formula is:

[0051]

[0052] The preparation method of the p-methoxy trifluoroacetophenone of the present embodiment, comprises the following steps:

[0053] 1) P-methoxybenzaldehyde, Li 2 CO 3 Dissolve in DMF according to the molar ratio of 20:1, and put it into a three-neck glass bottle together with the magnet, and repeatedly vacuumize and flush it into N 2 After 4 times, the three-neck glass bottle was placed in an ice bath and stirred vigorously; the amount of DMF was 5L of DMF per mole of p-methoxybenzaldehyde;

[0054] 2) When the temperature in step 1) drops to -3°C, slowly add trifluoromethyl trimethyl silicon dropwise according to the molar ratio of p-methoxybenzaldehyde: trifluoromethyl trimethyl silicon 1:2.5 ; After dropping the trifluoromethyl ketone for 20 minutes, the temperature was raised to room te...

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Abstract

The present invention discloses an aromatic ring or a heteroaromatic trifluoromethyl ketone compound and a preparation method thereof, and belongs to the technical field of organic synthesis. In the present invention, aromatic ring or heteroaromatic formaldehyde and trifluoromethyl trimethylsilane as raw materials to synthesize the corresponding a substituted trifluoromethyl alcohol compound, then the trifluoromethyl alcohol compound is oxidized to obtain an aromatic ring or a heteroaromatic trifluoromethyl ketone compound. The method is simple to operate, easy in purification, high in yield, and small in needed oxidant equivalent, and has a wide promotional value. The trifluoromethyl ketone compound prepared by the invention can used as an inhibitor, also is an important intermediate for synthesizing trifluoromethyl-substituted heterocyclic compounds and other compounds, and is a monomer for novel polymer materials. The trifluoromethyl ketone compound prepared by the present invention therefore has wide application range.

Description

technical field [0001] The invention relates to an aromatic ring or aromatic heterocyclic trifluoromethyl ketone compound and a preparation method of the compound, belonging to the technical field of organic synthesis. Background technique [0002] Among many trifluoromethyl compounds, trifluoromethyl ketone occupies a very important position, and it is a key component of important biologically active molecules. Since the trifluoromethyl group in trifluoromethyl ketone has a strong electron-withdrawing effect, it can make trifluoromethyl ketone compounds have abnormal nucleophilicity. At present, the stable hydrated form of trifluoromethyl ketones and their related tetrahedral structure properties have been developed as a large number of enzyme inhibitors; trifluoromethyl ketones are also used to synthesize trifluoromethyl-substituted heterocycles and other compounds It is an important intermediate; at the same time, it is also a monomer of new polymer materials. Therefore...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/06C07C45/29C07C49/80C07C49/84C07C49/235C07C49/788C07C221/00C07C225/22C07C205/45C07C201/12C07C255/56C07C253/30C07D213/61C07D209/12C07D307/46C07D333/56C07D333/28C07D307/80C07D319/18
Inventor 吴豫生邹大鹏李敬亚郭瑞云高剑昕程辉成牛成山
Owner TETRANOV PHARMA CO LTD
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