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Perfluoro alkoxylation reagent and preparation method and application thereof

A perfluoroalkoxy and alkyl technology is used in the preparation of trifluoromethoxy ester compounds. The trifluoromethoxyl group is introduced into the field of organic molecules by trifluoromethoxyl group, which can solve the problem of trifluoromethoxyl group. Difficulty in oxygen groups, scarcity of trifluoromethoxylation reagents, inconvenient operation and use, etc.

Active Publication Date: 2018-09-11
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the introduction of trifluoromethoxy is a very difficult thing, and trifluoromethoxyl reagents are very rare
What have practical value in bibliography at present has only following kind of reagent, and the one, trifluoromethyl trifluoromethanesulfonate (TFMT) can release trifluoromethoxy anion, realizes such as the reaction of types such as nucleophilic substitution reaction, but this The reagent is a liquid reagent, and the boiling point is only 19°C, which is inconvenient to operate and use
The second is benzenesulfonic acid trifluoromethyl ester reagents, which can realize the asymmetric trifluoromethoxy bromination reaction of alkenes, but it is prepared by corresponding benzenesulfonic acid and expensive togni reagent, and the cost is too high

Method used

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  • Perfluoro alkoxylation reagent and preparation method and application thereof
  • Perfluoro alkoxylation reagent and preparation method and application thereof
  • Perfluoro alkoxylation reagent and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0143]

[0144] KF (65.4g, 1125mmol) and 18-crown-6 (8.9g, 34mmol) were added to the 350mL sealed tube I equipped with a strong stirring bar baked by a heat gun, and in the glove box. The glove box was removed, 230 mL of acetonitrile was added under nitrogen protection, and triphosgene (37.1 g, 125 mmol) was added under cooling in a dry ice / acetone bath, the temperature was raised to room temperature, and the reaction was carried out at room temperature for 1 hour. In another 350mL sealed tube II with a strong stirrer that has been baked by a heat gun, add KF (2.2g, 38mmol), 18-crown-6 (9.9g, 38mmol) and 100mL dry THF in the glove box, remove glove box. Pump the sealing tube II for 1-2 seconds to negative pressure, and then seal the mouth. Connect the sealed tube I and the sealed tube II through a catheter. At this time, the sealed tube I is heated to 80°C, and the sealed tube II is cooled to 78°C in a dry ice / acetone bath, and then the sealed tube is opened to transfer fluo...

Embodiment 2

[0147]

[0148] KF (65.4g, 1125mmol) and 18-crown-6 (9.3g, 35mmol) were added to the 350mL sealed tube I equipped with a strong stirring bar baked by a heat gun, and in the glove box. The glove box was removed, 230 mL of acetonitrile was added under nitrogen protection, and triphosgene (37.1 g, 125 mmol) was added under cooling in a dry ice / acetone bath, the temperature was raised to room temperature, and the reaction was carried out at room temperature for 1 hour. In another 350mL sealed tube II equipped with a strong stirring bar baked by a heat gun, add TBAT (40.5g, 75mmol) and 100mL dry tetrahydrofuran into the glove box, and remove it from the glove box. Pump the sealing tube II for 1-2 seconds to negative pressure, and then seal the mouth. Connect the sealed tube I and the sealed tube II through a catheter. At this time, the sealed tube I is heated to 80°C, and the sealed tube II is cooled to 78°C in a dry ice / acetone bath, and then the sealed tube is opened to transf...

Embodiment 3

[0151]

[0152] Add NaF (1.26g, 30mmol) to the 10mL sealed tube I equipped with a strong stirrer that has been baked by a heat gun, and in the glove box. Remove the glove box, add Ishikawa's Reagent (6.69g, 30mmol) under nitrogen protection, add trifluoroacetic acid (1.71g, 15mmol) under cooling in a dry ice / acetone bath, warm to room temperature, and react at room temperature for 2 hours. Add TBAT (2.43g, 4.5mmol) and 6mL dry tetrahydrofuran to another 10mL sealed tube II equipped with a strong stirrer that has been baked by a heat gun, and remove it from the glove box. Pump the sealing tube II for 1-2 seconds to negative pressure, and then seal the mouth. Connect the sealed tube I and the sealed tube II through a catheter. At this time, the sealed tube I is heated to 50°C, and the sealed tube II is cooled to 78°C in a dry ice / acetone bath, then the sealed tube is opened, and the trifluoroacetyl fluoride is transferred from the sealed tube I to In Lock II, it took 2 hours...

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PUM

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Abstract

The invention provides a perfluoro alkoxylation reagent and a preparation method and application thereof. Specifically, the provided perfluoro alkoxylation reagent shown as a formula A can be used fornormal perfluoro alkoxylation reactions in the field, especially trifluoromethylation. Raw materials related to the perfluoro alkoxylation reagent are low in price and easy to obtain, the reaction condition is mild, the operation is simple, the cost is low, and the reagent is easy to popularize and suitable for large-scale production. The formula A is as shown in the description.

Description

technical field [0001] The invention belongs to the field of organic synthesis. Specifically, the present invention relates to a preparation method and application of a trifluoromethoxylating reagent, more specifically, to a preparation method of trifluoromethoxy ester compounds, and as a Use of trifluoromethoxylating reagents to introduce trifluoromethoxy groups into organic molecules. Background technique [0002] The introduction of fluorine atoms in organic compounds can dramatically change the electronic effect, steric effect and lipid solubility of the compound molecules. People have developed a large number of methods and reagents, and realized the synthesis of many fluorine-containing compounds. Among all the studied fluorine-containing groups, trifluoromethoxy is called the "least familiar" fluorine-containing group. The introduction of this group can effectively improve the biological activity of the molecule, but little is known about this group. Research introd...

Claims

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Application Information

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IPC IPC(8): C07C67/14C07C69/78C07C41/01C07C43/225C07C43/174C07D317/64C07D209/12C07D209/08C07J43/00C07C46/00C07C50/28C07D275/06C07H1/00C07H15/04C07D493/14C07D249/08C07C29/68C07C31/40
CPCC07C29/68C07C31/40C07C41/01C07C43/1742C07C43/225C07C46/00C07C50/28C07C67/14C07C69/78C07D209/08C07D209/12C07D249/08C07D275/06C07D317/64C07D493/14C07H1/00C07H15/04C07J43/003C07C2602/08
Inventor 胡金波周敏倪传法
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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