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Ortho-trifluoropropinylphenol compounds and preparation method thereof

A technology for trifluoropropynyl phenol and compounds, which is applied in the field of ortho-trifluoropropynyl phenol compounds and their preparation, can solve the problems of few reports, no methods for synthesizing such compounds, and no applications. Achieve the effects of good stability, high yield and mild synthesis conditions

Inactive Publication Date: 2008-09-17
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although ortho alkynyl phenols are widely used, ortho trifluoropropynyl phenols are not used in this respect, and there are few reports about such compounds (Bull Chem.Soc.Jpn., 1990, 63 , 2124), and there is no publicly reported method for synthesizing this type of compound

Method used

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  • Ortho-trifluoropropinylphenol compounds and preparation method thereof
  • Ortho-trifluoropropinylphenol compounds and preparation method thereof
  • Ortho-trifluoropropinylphenol compounds and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0019] The general structural formula is I, wherein, R 1 , R 2 Preparation of the phenolic compound 2-(3,3,3-trifluoropropynyl)phenol as H.

[0020] Dissolve 1 mL of the compound salicylaldehyde in 10 mL of N,N-dimethylformamide, protect it under a nitrogen balloon, and at room temperature, add 3.25 g of zinc powder, 2.8 mL of acetic anhydride, stir, and add 1,1 , 1-trichloro-2,2,2-trifluoroethane 3.6mL, after the dropwise addition, continue to react for 3 hours, add 50mL saturated ammonium chloride solution and 50mL ethyl acetate, separate liquid, ethyl acetate extract water layer, the organic phase was collected and concentrated, and the resulting dark brown liquid was separated and purified by flash column chromatography using petroleum ether as the eluent to obtain 1.32 g of light brown liquid, with a yield of 50%. Dissolve this compound in 50mL of ether, add 1.68g of potassium tert-butoxide at room temperature, react for 3 hours, add 50mL of saturated ammonium chloride ...

Embodiment 2

[0023] The general structural formula is I, wherein, R 1 for CH 3 , R 2 Preparation of the phenolic compound 4-methyl-2-(3,3,3-trifluoropropynyl)phenol as H.

[0024] Dissolve 1.36g of the compound 5-methylsalicylaldehyde in 15mL of N,N-dimethylformamide, under nitrogen balloon protection, at room temperature, add 3.25g of zinc powder, 2.8mL of acetic anhydride, stir, and drop into it Add 3.6mL of 1,1,1-trichloro-2,2,2-trifluoroethane, after the dropwise addition, continue to react for 3 hours, add 75mL of saturated ammonium chloride solution and 75mL of ethyl acetate, separate liquid, acetic acid The aqueous layer was extracted with ethyl ester, the organic phase was collected and concentrated, and the resulting brown liquid was separated and purified by flash column chromatography using petroleum ether as an eluent to obtain 1.25 g of a light brown liquid with a yield of 45%. Dissolve this compound in 30 mL of ether, add 1.51 g of potassium tert-butoxide, react for 3 hour...

Embodiment 3

[0027] The general structural formula is I, wherein, R 1 for Cl, R 2 Preparation of the phenolic compound 4-chloro-2-(3,3,3-trifluoropropynyl)phenol as H.

[0028] Dissolve 1.57g of the compound 5-chlorosalicylaldehyde in 15mL of N,N-dimethylformamide, under nitrogen balloon protection, at room temperature, add 3.25g of zinc powder, 2.8mL of acetic anhydride, stir, and dropwise add 1,1,1-Trichloro-2,2,2-Trifluoroethane 3.6mL, after dropwise addition, continue to react for 4 hours, add 75mL saturated ammonium chloride solution and 75mL ethyl acetate, separate liquid, ethyl acetate The aqueous layer was extracted with ester, and the organic phase was collected and concentrated. The resulting brown liquid was separated and purified by flash column chromatography using petroleum ether as the eluent to obtain 1.31 g of a light yellow solid with a yield of 44%. Dissolve this compound in 40mL of ether, add 1.48g of potassium tert-butoxide at room temperature, react for 5 hours, add...

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Abstract

The invention relates to vicinal trifluoro propinyl phenol compound and a preparation method thereof. More particularly, the method has a structural general formula shown in a right formula, wherein, R<1> is selected from H, CH3, Cl or Br; R<2> is selected from H or OCH3. The vicinal trifluoro propinyl phenol compound which is compounded by the method is an important precursor for compoundings a polysubstituted benzofuran derivative, a polysubstituted benzfuran derivate in a furan ring can be obtained through palladium-catalyzed ring formation, and a three-position iodo-benzfuran derivate can be also obtained through iodine cyclization. In the method of compounding the vicinal trifluoro propinyl phenol compound, the raw material is easily obtained, the compounding technology is simple and easy to implement, and the productive rate is high.

Description

technical field [0001] The invention relates to an ortho-trifluoropropynyl phenol compound and a preparation method thereof. technical background [0002] Ortho-alkynylphenols are currently the most widely used intermediates in the synthesis of benzofuran derivatives. Starting from ortho-alkynyl phenol, 2-substituted and 2,3-disubstituted benzofuran derivatives can be easily obtained under the catalysis of palladium; this method can be used in combinatorial chemistry to obtain a series of benzofuran derivatives conveniently and quickly. and furan compound library. Under the action of iodine, ortho-alkynyl phenol and ortho-alkynyl phenyl methyl ether can be transformed into benzofuran derivatives whose 3-position is substituted by iodine. Although ortho alkynyl phenols are widely used, ortho trifluoropropynyl phenols are not used in this respect, and there are few reports about such compounds (Bull Chem.Soc.Jpn., 1990, 63 , 2124), and there is no publicly reported method f...

Claims

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Application Information

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IPC IPC(8): C07C39/24C07C39/18C07C37/20C07C43/23C07C41/30
Inventor 徐经伟周华牛佳佳李志刚
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI