Fluorination method

A technology of fluorination and fluorination reagents, applied in organic chemistry methods, chemical instruments and methods, organic chemistry and other directions, can solve the problems of low stability and high cost, and achieve the effect of good yield and high tolerance

Pending Publication Date: 2021-01-05
SANMING HEXAFLUO CHEM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Aiming at the problems of high cost and low stability of existing fluorinating reagents used to prepare ac

Method used

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Examples

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Example Embodiment

[0047]The fluorinating reagent can be prepared by an existing preparation method:

[0048]For example, in some embodiments, the perfluoropolyether chain carboxylate provided by the present invention can be prepared by reacting a perfluoropolyether chain carboxylate with a base.

[0049]In some embodiments, the molar ratio of the substrate to the fluorinating reagent is 1:0.25-2.

[0050]In some embodiments, the fluorination reaction is performed in an organic solvent system.

[0051]In some embodiments, the reaction temperature of the fluorination reaction is 50°C to 150°C.

[0052]In some embodiments, when the substrate is selected from carboxylic acid compounds, the fluorination reaction is carried out in an organic solvent, the reaction temperature is 50°C to 135°C, and the molar ratio of the substrate to the fluorinating reagent is 1:0.5 to 2.

[0053]In a preferred embodiment, when the substrate is selected from carboxylic acid compounds, the organic solvent is selected from organic polar solven...

Example Embodiment

[0075]Example 1

[0076]CF3OCF2OCF2CO2K is an example to illustrate the preparation method of perfluoropolyether chain carboxylate provided by the present invention, including the following operations:

[0077]Add CF to a 500mL single-neck bottle3OCF2OCF2CO2C2H5(54.8g, 0.2mol) and 150mL of ethanol. Dissolve KOH (10.1g, 0.18mol) in 10mL of water. Use a syringe to add the KOH aqueous solution dropwise to the single-necked flask. After the addition, stir vigorously and react at room temperature overnight. . After the reaction, the solvent was removed under reduced pressure, and the water was removed by pumping with an oil pump overnight under heating at 50°C to obtain 55.7 g of white solid CF3OCF2OCF2CO2K.

[0078]The specific reaction formula is as follows:

[0079]

[0080]Hereinafter, the present invention will be further illustrated by the fluorination reaction example of carboxylic acid compound.

Example Embodiment

[0081]Example 2

[0082]This embodiment is used to illustrate the fluorination method disclosed in the present invention, including the following steps:

[0083]Weigh carboxylic acid substrate 4-1a (0.2mmol, 1.0equiv) and fluorinating reagent CF in a 10mL dried Shrek tube3OCF2OCF2CO2K (0.2 mmol, 1.0 equiv), pump nitrogen for three times, add 1 mL of anhydrous acetonitrile under the protection of nitrogen, and react at 80° C. for 1 h. After the reaction, it was cooled to room temperature to obtain the reaction product. The reaction product was purified by filtration through a silica gel plug. The silica gel plug was washed with a mixture of petroleum ether / ethyl acetate (150ml; 20:1~5:1, v:v), and the filtrate was spin-dried to dry the solvent. The final product 4-2a is obtained.

[0084]The specific reaction formula is as follows:

[0085]

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Abstract

In order to overcome the problems of high cost and low stability of the existing fluorination reagents for preparing acyl fluoride, sulfonyl fluoride and phosphoryl fluoride compounds, the invention provides a fluorination method, which comprises the following operation steps of: adding a fluorination reagent into a substrate, wherein the fluorination reagent comprises cations M and anions, the anions are selected from one or more of perfluoropolyether chain carboxylic acid anions as shown in the specification: CF3(OCF2)nCO2<->, wherein n is selected from 1-10; the substrate comprises a carboxylic acid compound, a sulfonic acid compound, a phosphoric acid compound and a phosphine oxide compound; and carrying out fluorination reaction to obtain acyl fluoride, sulfonyl fluoride and phosphoryl fluoride products. According to the fluorination method provided by the invention, the perfluoropolyether chain carboxylate is used as a fluorination reagent, so that the dehydroxylation fluorination reaction of the carboxylic acid compound, the sulfonic acid compound and the phosphoric acid compound and the fluorination reaction of the phosphine oxide compound are realized, the product yield isrelatively high, and the fluorination method has relatively good universality for different substrates.

Description

technical field [0001] The invention belongs to the technical field of fluorination, and in particular relates to a fluorination method. Background technique [0002] Acyl fluoride (-COF), sulfonyl fluoride (-SO 2 F) and phosphoryl fluoride compounds (-POF) are important synthetic building blocks in the field of organic synthesis, and have many applications in the fields of synthesis, materials and biology. Among them, acyl fluoride, as the key synthetic building block in the synthesis, has been used as an acylating agent for various nucleophilic molecules, which can efficiently convert carbon-fluorine bonds (C-F) into carbon-carbon bonds, carbon-oxygen bonds, carbon-nitrogen bonds and carbon-sulfur bonds, etc. As the key group of the second generation of click chemistry (SuFEx Click Chemistry), fluorosulfonyl is playing an increasingly important role in materials chemistry, medicinal chemistry, and organic synthesis chemistry. Phosphoryl fluoride compounds are a class of...

Claims

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Application Information

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IPC IPC(8): C07B39/00C07C51/60C07C63/36C07C63/10C07C253/30C07C255/57C07C63/70C07C65/21C07C63/64C07C201/12C07C205/58C07C53/50C07C57/68C07C59/64C07C61/135C07D319/20C07D207/34C07D209/42C07D271/12C07D231/16C07D311/12C07C57/72C07C303/40C07C311/16C07J9/00C07C303/02C07C309/86C07C309/80C07F9/34
CPCC07B39/00C07C51/60C07C253/30C07C201/12C07D319/20C07D207/34C07D209/42C07D271/12C07D231/16C07D311/12C07C303/40C07J9/005C07C303/02C07F9/34C07C2602/10C07C2602/42C07C2603/74C07C63/36C07C63/10C07C255/57C07C63/70C07C65/21C07C63/64C07C205/58C07C53/50C07C57/68C07C59/64C07C61/135C07C57/72C07C311/16C07C309/86
Inventor 吕涛赵世玉郭勇吴成英曹伟陈庆云王孟英
Owner SANMING HEXAFLUO CHEM CO LTD
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