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Preparation method of trifluoromethyl chromone compound

A technology of trifluoromethyl chromone and trifluoromethylation, which is applied in the field of preparation of trifluoromethyl chromone compounds, can solve the problems of unsuitability for industrialization and high cost, and achieve creative effects

Pending Publication Date: 2020-12-15
浙江瑞博制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The problem to be solved by the present invention is to provide a method for trifluoromethylation of hydroxyaromatic enaminoketones, thereby solving the problems of high cost and unsuitability for industrialization of existing methods

Method used

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  • Preparation method of trifluoromethyl chromone compound
  • Preparation method of trifluoromethyl chromone compound
  • Preparation method of trifluoromethyl chromone compound

Examples

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Embodiment 1

[0022]

[0023] Under nitrogen protection, add 1.0mmol 1a, 1.2mmol Umeben's reagent 2a, 5mL DMF, and 1.5mmol DMAP into a 10mL reaction tube. Placed in an oil bath at 80°C for 3h, then moved to room temperature. Add 20 mL of water, extract with ethyl acetate three times (25 mL×3), combine the ethyl acetate layers, wash with water three times (20 mL×3), and dry over anhydrous magnesium sulfate. Suction filtration, concentration to dryness under reduced pressure, and purification by column chromatography gave the target product with a yield of 75%.

Embodiment 2

[0025]

[0026] Under nitrogen protection, add 1.0mmol 1a, 1.2mmol Umeben's reagent 2a, 5mL CH 3 CN, 1.5 mmol DMAP. Placed in an oil bath at 80°C for 3h, then moved to room temperature. Add 20 mL of water, extract with ethyl acetate three times (25 mL×3), combine the ethyl acetate layers, wash with water three times (20 mL×3), and dry over anhydrous magnesium sulfate. Suction filtration, concentration to dryness under reduced pressure, and purification by column chromatography gave the target product with a yield of 65%.

Embodiment 3

[0028]

[0029] Under nitrogen protection, add 1.0mmol 1a, 1.2mmol Umeben's reagent 2a, 5mL DMSO, 1.5mmol DMAP into a 10mL reaction tube. Placed in an oil bath at 80°C for 3h, then moved to room temperature. Add 20 mL of water, extract with ethyl acetate three times (25 mL×3), combine the ethyl acetate layers, wash with water three times (20 mL×3), and dry over anhydrous magnesium sulfate. Suction filtration, concentration to dryness under reduced pressure, and purification by column chromatography gave the target product with a yield of 55%.

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Abstract

The invention discloses a preparation method of a trifluoromethyl chromone compound, which is prepared by carrying out trifluoromethylation and cyclization reaction on a compound as shown in a formulaI in the presence of organic alkali without irradiation of visible light to initiate reaction or action of a photo-catalyst. Compared with the prior art, the method has the advantages of simple operation, safety, reliability, easy amplification, environmental friendliness and the like. R is a mono-substituted or multi-substituted group at any position on a benzene ring, and can be halogen, alkyl,alkoxy and the like in the same or different manner.

Description

technical field [0001] The invention relates to a method for preparing trifluoromethyl chromone compounds, in particular to a method for preparing trifluoromethyl chromone compounds by trifluoromethylation reaction. Background technique [0002] Trifluoromethylchromones have been reported in detail in journal literature, see Organic Letters, Volume: 19, Issue: 1, Pages: 146-149, 2017. The journal literature also discloses the preparation method of trifluoromethyl chromone compounds. Under the irradiation of visible light, under the action of photocatalyst, trifluoromethyl chromone compounds are prepared by trifluoromethylation reaction. Ketones. [0003] [0004] The photocatalyst used in this method is very expensive, which is not conducive to industrial scale-up production. In addition, although there are records in the journal literature that commonly used fluoromethylation reagents, such as: BrCF 2 COR, Langlois / Togni / Umemoto, but just citing other literature that ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/22
CPCC07D311/22
Inventor 周晓聪何鑫奕华允宇严普查李原强
Owner 浙江瑞博制药有限公司
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