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Method for synthetizing 2-fluoro phenol compound

A technology of phenolic compounds and fluorophenols, which is applied in the field of synthesizing 2-fluorophenolic compounds, and can solve problems such as unreported phenolic compounds

Active Publication Date: 2015-08-19
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the carbon-hydrogen bond fluorination of phenolic compounds has not been reported

Method used

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  • Method for synthetizing 2-fluoro phenol compound
  • Method for synthetizing 2-fluoro phenol compound
  • Method for synthetizing 2-fluoro phenol compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050]

[0051] [1] 1.57g (10.0mmol) of 2-bromopyridine, 0.10g (0.5mmol) of cuprous iodide, 0.124g (0.1mmol) of pyridine-2-carboxylic acid, 4.240g (20.0mmol) of tripotassium phosphate, 1.128 phenol g (12.0mmol), and 20ml DMSO were added to a 100ml flask. The mixture was heated to 80°C for 24 hours under the protection of nitrogen, and TLC detected that the reaction was complete. Add 50ml of ethyl acetate to dilute, wash and extract, take the organic phase and dry it, remove the solvent under reduced pressure, and the residue is subjected to column chromatography [GF254 silica gel; 100 -200 mesh; Developing agent is V (petroleum ether) / V (ethyl acetate)=10 / 1] separation and purification, collection contains the eluent of product, eluent evaporates solvent and obtains 2-phenoxypyridine 1.368 g (80% yield).

[0052] [2] Add 2-phenoxypyridine (0.855g, 5.0mmol), bis(dibenzylideneacetone)palladium (143.8mg, 0.25mmol), N-fluorobisbenzenesulfonamide into a closed reaction vessel ...

Embodiment 2

[0055]

[0056] [1] 1.57g (10.0mmol) of 2-bromopyridine, 0.10g (0.5mmol) of cuprous iodide, 0.124g (0.1mmol) of pyridine-2-carboxylic acid, 4.240g (20.0mmol) of tripotassium phosphate, 2- Chlorophenol 1.524g (12.0mmol), and 20ml DMSO were added to a 100ml flask. The mixture was heated to 80°C for 24 hours under the protection of nitrogen, and TLC detected that the reaction was complete. Add 50ml of ethyl acetate to dilute, wash and extract, take the organic phase and dry it, remove the solvent under reduced pressure, and the residue is subjected to column chromatography [GF254 silica gel; 100 -200 mesh; Developing agent is V (petroleum ether) / V (ethyl acetate)=10 / 1] separation and purification, collection contains the eluent of product, eluent evaporates solvent and obtains 2-(2-chlorobenzene Oxy)pyridine 1.66 g (81% yield).

[0057] [2] Add 2-(3-chlorophenoxy)pyridine (1.025g, 5.0mmol), bis(dibenzylideneacetone)palladium (143.8mg, 0.25mmol), N-fluoro Diphenylsulfonamide ...

Embodiment 3

[0060]

[0061][1] 1.57g (10.0mmol) of 2-bromopyridine, 0.10g (0.5mmol) of cuprous iodide, 0.124g (0.1mmol) of pyridine-2-carboxylic acid, 4.240g (20.0mmol) of tripotassium phosphate, 4- Add 1.296g (12.0mmol) of methylphenol and 20ml DMSO into a 100ml flask. The mixture was heated to 80°C for 24 hours under the protection of nitrogen, and TLC detected that the reaction was complete. Add 50ml of ethyl acetate to dilute, wash and extract, take the organic phase and dry it, remove the solvent under reduced pressure, and the residue is subjected to column chromatography [GF254 silica gel; 100 -200 mesh; Developing agent is V (petroleum ether) / V (ethyl acetate)=10 / 1] separation and purification, collection contains the eluent of product, and eluent evaporates solvent to obtain 2-(4-methyl Phenoxy)pyridine 1.54 g (83% yield).

[0062] [2] Add 2-(4-methylphenoxy)pyridine (0.925g, 5.0mmol), bis(dibenzylideneacetone)palladium (143.8mg, 0.25mmol), N- Fluorobisbenzenesulfonamide (1....

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Abstract

The present invention provides a method for synthetizing a 2-fluoro phenol compound shown in a formula IV. The phenol compound shown in the formula I is prepared into a 2-pyridine oxygroup arene compound shown in a formula II through an Ullmann reaction, the 2-pyridine oxygroup arene compound shown in the formula II is mixed with a palladium catalyst, a fluorinating reagent, an additive and an organic solvent, the mixture is stirred under the temperature of 30-160 DEG C to perform a fluorination reaction to obtain an ortho-position fluoridated 2-pyridine oxygroup arene compound shown in a formula III, and the ortho-position fluoridated 2-pyridine oxygroup arene compound shown in the formula III is prepared into the 2-fluoro phenol compound shown in the formula IV through the action of alkali. The method provided by the present invention has the advantages of mild reaction conditions, simplicity in operations, good substrate adaptability, high fluorination selectivity and the like. The 2-fluoro phenol compound is shown in the figure below.

Description

technical field [0001] The invention relates to a method for synthesizing 2-fluorophenol compounds. Background technique [0002] The introduction of fluorine atoms into aromatic hydrocarbon compounds can significantly increase the stability of the compound, and at the same time improve its fat solubility and hydrophobicity, promote its absorption and delivery in the body, and change the physiological effects, so many fluorine-containing medicines and pesticides are in performance. Relatively, it has the characteristics of less dosage, low toxicity, high drug efficacy, and strong metabolism, which makes it account for an increasing proportion of new medicines and pesticides. In addition, fluorine-containing dyes, fluorine-containing surfactants, fluorine-containing fabric finishing agents, and fluorine-containing coatings have become high value-added and promising varieties in the field of fine chemicals. It is precisely because of the particularity of carbon-fluorine bonds...

Claims

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Application Information

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IPC IPC(8): C07B41/02C07C37/055C07C39/27C07C39/28C07C39/367C07C41/26C07C43/23C07C201/12C07C205/26C07C45/64C07C49/825C07D215/20
CPCY02P20/52
Inventor 娄绍杰许丹倩徐振元
Owner ZHEJIANG UNIV OF TECH
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