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Synthesis method of beta-trifluoromethyl substituted alcohol organic molecule

A technology of trifluoromethyl and synthetic methods, which is applied in the field of synthesis of alcohol organic molecules, can solve problems such as limited synthetic routes and lack of research on trifluoromethyl hydroxylation, and achieves reduced synthesis costs, high yields, and low reaction rates. The effect of simple system components

Active Publication Date: 2020-05-15
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But at the same time, studies on the trifluoromethyl hydroxylation of alkenes are very scarce, and the synthetic routes of alcohol organic molecules substituted with trifluoromethyl at the β position are very limited.

Method used

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  • Synthesis method of beta-trifluoromethyl substituted alcohol organic molecule
  • Synthesis method of beta-trifluoromethyl substituted alcohol organic molecule
  • Synthesis method of beta-trifluoromethyl substituted alcohol organic molecule

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Take a washed and dried pressure-resistant tube, add a magnet, then weigh 0.2mmol p-tert-butylstyrene, 0.4mmol sodium trifluoromethanesulfinate, 0.1M lithium perchlorate, and start stirring. While stirring, 4 ml of ethylene glycol dimethyl ether was added, followed by the slow addition of 0.4 ml of trifluoroacetic acid. Then insert the counter electrode, connect and turn on the power supply, set the constant current mode, the current size is 15mA, and react at room temperature for 6 hours. After the reaction was completed, the reaction solution was poured into saturated brine, extracted three times with dichloromethane (30ml×3), dried over anhydrous sodium sulfate, filtered, rotary evaporated, loaded, and subjected to column chromatography to obtain the final product. Trifluorotoluene was used as a calibration substance, and its concentration was calibrated by fluorine spectrum, and the yield was about 90%.

Embodiment 2

[0031] Take a washed and dried pressure-resistant tube, add a magnet, then weigh 0.2mmol of p-methylstyrene, 0.4mmol of sodium trifluoromethanesulfinate, and 0.1M lithium perchlorate in turn, start stirring, and 4 ml of ethylene glycol dimethyl ether was added with stirring, followed by the slow addition of 0.4 ml of trifluoroacetic acid. Then insert the counter electrode, connect and turn on the power supply, set the constant current mode, the current size is 15mA, and react at room temperature for 6 hours. After the reaction was completed, the reaction solution was poured into saturated brine, extracted three times with dichloromethane (30ml×3), dried over anhydrous sodium sulfate, filtered, rotary evaporated, loaded, and subjected to column chromatography to obtain the final product. Trifluorotoluene was used as a calibration substance, and its concentration was calibrated by fluorine spectrum, and the yield was about 92%.

Embodiment 3

[0038]Take a washed and dried pressure-resistant tube, add a magnet, then weigh 0.2mmol p-chlorostyrene, 0.4mmol sodium trifluoromethanesulfinate, 0.1M lithium perchlorate, start stirring, and stir While adding 4ml of ethylene glycol dimethyl ether, then slowly added 0.4ml of trifluoroacetic acid. Then insert the counter electrode, connect and turn on the power supply, set the constant current mode, the current size is 15mA, and react at room temperature for 6 hours. After the reaction was completed, the reaction solution was poured into saturated brine, extracted three times with dichloromethane (30ml×3), dried over anhydrous sodium sulfate, filtered, rotary evaporated, loaded, and subjected to column chromatography to obtain the final product. Trifluorotoluene was used as a calibration substance, and its concentration was calibrated by fluorine spectrum, and the yield was about 94%.

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Abstract

The invention discloses a synthesis method of a beta-trifluoromethyl substituted alcohol organic molecule. The method comprises the following steps: firstly, mixing a styrene substrate, sodium trifluoromethanesulfinate and an electrolyte salt lithium perchlorate; adding a solvent ethylene glycol dimethyl ether and a strong acid trifluoroacetic acid while stirring, then inserting a counter electrode below the liquid level of the solvent, and carrying out an electrocatalytic reaction under the conditions of constant current of 15 + / -3 mA and stirring to obtain the beta-trifluoromethyl substituted alcohol organic molecule corresponding to the substrate. The beta-trifluoromethyl substituted alcohol organic molecule is synthesized by using an electro-catalysis means, and an active intermediateis generated through direct initiation of single electron transfer, so the use of a metal catalyst and a peroxidant is avoided, the reaction system is green and efficient, and a practical and effective path is provided for the synthesis of the beta-trifluoromethyl substituted alcohol organic molecule.

Description

technical field [0001] The invention relates to a method for synthesizing an alcohol organic molecule substituted by a β-position trifluoromethyl group, and belongs to the technical field of organic chemical synthesis. Background technique [0002] The atomic radius of the fluorine atom is small, and the Van der Hual radius is only Smaller than all other carbon-halogen bonds, it is often used in medicinal chemistry to replace C-H, -OH, etc. to modify molecules; the electronegativity of fluorine is 3.98, which is the element with the highest electronegativity, and the dipole of the carbon-fluorine bond The moment is as high as 1.41D; the bond energy of the C-F bond is also as high as 480kJ / mol, and the bond length is only This makes fluorine-containing organics highly thermally and chemically stable. Since the bond energy of the C-F bond is higher than that of the C-H bond, in medicinal chemistry, using fluorine atoms to selectively block the easily metabolizable position...

Claims

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Application Information

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IPC IPC(8): C25B3/02C25B3/23
CPCC25B3/23
Inventor 易文斌路俊欣蒋绿齐
Owner NANJING UNIV OF SCI & TECH
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