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A kind of method of ortho position direct fluorination of phenolic compound

A technology of phenolic compounds and compounds, which is applied in the field of direct fluorination of phenolic compounds, can solve the problems of reducing the research progress of modification of phenolic compounds, many method steps, and low reaction yield, and achieves mild reaction conditions and easy operation. Simple process and efficient response

Active Publication Date: 2022-05-20
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The conditions of this kind of method are relatively harsh, and there are many steps in the method, and the reaction yield is low. These problems have greatly reduced the progress of the research on the modification of phenolic compounds.

Method used

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  • A kind of method of ortho position direct fluorination of phenolic compound
  • A kind of method of ortho position direct fluorination of phenolic compound
  • A kind of method of ortho position direct fluorination of phenolic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1: the preparation of compound 2A-1

[0041]

[0042] Add 1mmol of p-3-fluorophenol to 4ml of 10% (v / v) acetic acid aqueous solution, add 1.5mmol Selectfluor, 0.05mmol Eosin Y to it, and react under 12W blue light irradiation for 6 hours at room temperature. After the reaction, add saturated NaCl aqueous solution was extracted with dichloromethane, and the organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated to dryness under reduced pressure to obtain a crude compound. The crude compound was subjected to silica gel column chromatography, using a solution of ethyl acetate and petroleum ether with a volume ratio of 1:9 as the mobile phase, and the eluent with an Rf value of 0.3 to 0.5 was tracked and collected by TLC, and the collected eluent was passed through The solvent was removed under reduced pressure and dried to obtain 100 mg of the pure product of the compound represented by formula 2A-1 (yield 70%). For its H NMR spectrum...

Embodiment 2

[0043] Embodiment 2: the preparation of compound 2A-2

[0044]

[0045] Add 1mmol of p-phenol to 4ml of 10% acetic acid aqueous solution, add 1.5mmol Selectfluor, 0.05mmol Eosin Y to it, and react under 12W blue light irradiation at room temperature for 6 hours. After extraction, the organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated to dryness under reduced pressure to obtain the crude compound. The crude compound was subjected to silica gel column chromatography, using a solution of ethyl acetate and petroleum ether with a volume ratio of 1:9 as the mobile phase, and the eluent with an Rf value of 0.3-0.5 was tracked and collected by TLC, and the collected eluent was passed through The solvent was removed under reduced pressure and dried to obtain 90 mg (yield 77%) of the pure product of the compound shown in Formula 2A-2. For its H NMR, C, and F spectra, see Figure 4 ~ Figure 6 . 1 H NMR (500MHz, CDCl 3 )δ7.13(dt, J=8.2,1.4Hz,1H),7.03(ddd...

Embodiment 3

[0046] Embodiment 3: the preparation of compound 2A-3

[0047]

[0048]Add 1mmol 2-tert-butylphenol into 4ml of 10% acetic acid aqueous solution, add 1.5mmol Selectfluor, 0.05mmol Eosin Y therein, and react under 12W blue light irradiation at room temperature for 6 hours. After the reaction, add saturated NaCl aqueous solution to the reaction solution, and use Dichloromethane was extracted, and the organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated to dryness under reduced pressure to obtain the crude compound. The crude compound was subjected to silica gel column chromatography, using a solution of ethyl acetate and petroleum ether with a volume ratio of 1:9 as the mobile phase, and the eluent with an Rf value of 0.3-0.5 was tracked and collected by TLC, and the collected eluent was passed through The solvent was removed under reduced pressure and dried to obtain 120 mg (yield 73%) of the pure product of the compound shown in formula 2A-3. For ...

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Abstract

The invention relates to a method for direct fluorination of phenolic compounds at the ortho position, the method comprising: carrying out the phenolic compound shown in formula (1A) and a fluorinating reagent in a solvent at room temperature under the action of a photocatalyst and a light source reaction, after the reaction is complete, the reaction mixture is separated and purified to obtain fluorinated phenolic compounds shown in formula (2A); the beneficial effects of the present invention are mainly reflected in: the present invention provides a method for the direct fluorination of organic photocatalytic phenol, the operation process Simple, the raw materials are commercially available and easy to obtain, the photocatalyst is cheap, easy to obtain and environment-friendly, the reaction conditions are mild, the site selectivity is high, the reaction is efficient, and the fluorinated phenol derivatives can be prepared in one step.

Description

(1) Technical field [0001] The invention relates to a method for ortho-direct fluorination of phenolic compounds. (2) Background technology [0002] Phenol is an important basic organic raw material, and many of its downstream products are involved in many fields, mainly used in the manufacture of phenolic resin, bisphenol A and caprolactam. Phenol derivatives such as halogenated phenols, nitrophenols, and alkylphenols can be used in the production of medicines, pesticides, paints, dyes, explosives, and spices. Phenolic compounds widely exist in nature, and spices and many natural products contain phenolic structures. The traditional method for modifying phenolic compounds is: first protect the hydroxyl group, then modify other positions of the hydroxyl group, and finally deprotect to realize the modification. The conditions of this type of method are relatively harsh, and the method has many steps and the reaction yield is low. These existing problems have greatly reduced...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C37/62C07C39/27
CPCC07C37/62C07C39/27Y02P20/55
Inventor 朱勍刘江窦言东
Owner ZHEJIANG UNIV OF TECH
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