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A kind of fluoroalkyl ether copper (i) and its preparation method and application

A technology of fluoroalkyl ether and alkyl, which is applied in the field of fluoroalkyl ether copper (I) and its preparation and application, can solve the problems of poor substrate applicability, expensive fluorinating reagents, etc., and achieve good industrial Application prospects, the effect of simple operation

Inactive Publication Date: 2016-05-04
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Most of the existing trifluoroethoxylation or other fluoroalkyl ether reactions use excessive and expensive fluorinating reagents and catalysts, and the substrate applicability is not wide. Therefore, it is very necessary to develop a class of economical and efficient Trifluoroethoxylated or fluoroalkyl ether copper

Method used

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  • A kind of fluoroalkyl ether copper (i) and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0030] Add a polytetrafluoroethylene magnetic stirring bar into a 50mL single-necked flask, add 0.525mmol sodium tert-butoxide, 0.5mmol cuprous chloride and 25mL tetrahydrofuran solvent, mix well, react at room temperature for 1 hour under nitrogen protection, and filter the solution , to obtain a cuprous tert-butoxide solution; add a tetrahydrofuran solution containing 1.0 mmol 1,10-phenanthroline to the cuprous tert-butoxide solution, stir at room temperature for 10 min, add dropwise a tetrahydrofuran solution containing 0.5 mmol trifluoroethanol, and continue stirring After 5 minutes, the solution was filtered, and the solvent was removed under vacuum. The resulting solid was washed with ether and recrystallized to obtain a reddish-brown solid, which was 1,10-phenanthroline trifluoroethyl ether copper (I) complex.

[0031] figure 1 It is the single crystal structure of 1,10-phenanthroline and trifluoroethyl ether copper (I) complex, and its NMR data is: 1 H-NMR (400MHz, DM...

Embodiment 2

[0033] Add a polytetrafluoroethylene magnetic stirring bar into a 50mL single-necked flask, add 0.525mmol sodium tert-butoxide, 0.5mmol cuprous chloride and 25mL tetrahydrofuran solvent, mix well, react at room temperature for 1 hour under nitrogen protection, and filter the solution , to obtain a cuprous tert-butoxide solution; add a tetrahydrofuran solution containing 1.0 mmol 1,10-phenanthroline to the cuprous t-butoxide solution, stir at room temperature for 10 min, add dropwise a tetrahydrofuran solution containing 0.5 mmol tetrafluoropropanol, and continue Stir for 5 minutes, filter the solution, remove the solvent under vacuum, wash the obtained solid with ether, and recrystallize to obtain a reddish-brown solid, which is 1,10-phenanthroline tetrafluoropropyl ether copper (I) complex. Its NMR data are: 1 H-NMR (400MHz, DMSO) δ: 9.05 (s, 4H), 8.62 (d, J=8.0Hz, 4H), 8.09 (s, 4H), 7.85 (dd, J=7.0, 3.2Hz, 4H), 6.43 (t, J=52.4Hz, 1H), 3.81 (s, 2H). 19 F-NMR (376MHz, DMSO) ...

Embodiment 3

[0035] Add a polytetrafluoroethylene magnetic stirring bar into a 50mL single-necked flask, add 0.525mmol sodium tert-butoxide, 0.5mmol cuprous chloride and 25mL tetrahydrofuran solvent, mix well, react at room temperature for 1 hour under nitrogen protection, and filter the solution , to obtain a cuprous tert-butoxide solution; add a tetrahydrofuran solution containing 1.0 mmol 1,10-phenanthroline to the cuprous t-butoxide solution, stir at room temperature for 10 min, add dropwise a tetrahydrofuran solution containing 0.5 mmol pentafluoropropanol, and continue Stir for 5 minutes, filter the solution, remove the solvent under vacuum, wash the obtained solid with ether, and recrystallize to obtain a reddish-brown solid, which is 1,10-phenanthroline pentafluoropropyl ether copper (I) complex. Its NMR data are: 1 H-NMR (400MHz, DMSO) δ: 9.10 (s, 4H), 8.66 (d, J=8.0Hz, 4H), 8.14 (s, 4H), 7.91 (s, 4H), 3.99 (s, 2H). 19 F-NMR (376 MHz, DMSO) δ: -82.12 (s, 3F), -124.18 (s, 2F). 13...

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Abstract

The invention discloses fluoro alkyl ether copper (I), a preparation method of the fluoro alkyl ether copper (I) and an application of the fluoro alkyl ether copper (I) to fluoro alkyl etherification reaction. The fluoro alkyl ether copper (I) has a structural formula as shown in the specification, wherein RF is CF3, CF2CF3, CF2CHF2 or CF2CF2CF3, and R1 and R2 are H or alkyl independently. The fluoro alkyl ether copper (I) is prepared as follows: enabling cuprous chloride, sodium tert-butoxide, a nitrogen-nitrogen bidentate ligand and fluoro alkyl alcohol to react in a solvent of tetrahydrofuran, and then separating and purifying. The fluoro alkyl ether copper (I) is capable of promoting the fluoro alkyl etherification of a halogenated aromatic hydrocarbon and a halogenated heterocyclic compound efficiently to form an aromatic hydrocarbon or heterocycle containing fluoro alkyl ether derivative and has a good industrial application prospect.

Description

technical field [0001] The invention specifically relates to a fluoroalkyl ether copper (I) and its preparation method and its application in fluoroalkyl etherification reaction. Background technique [0002] Due to the high electronegativity and small atomic radius of fluorine atoms, fluorine-containing compounds exhibit unique physical and chemical properties, so they have very important applications in the fields of medicine, pesticides, and functional materials. Among the functional groups containing fluorine atoms, fluoroalkyl ethers (-OCH 2 R F ) Due to its strong electronegativity and strong lipophilicity, it has received a lot of attention, such as Silodosin (Silodosin) used to improve benign prostatic hyperplasia, antiarrhythmic drug Flecainide (Flecainide) and most other drug molecules Both contain trifluoroethoxy (-OCH 2 CF 3 ). [0003] Most of the existing trifluoroethoxylation or other fluoroalkyl ether reactions use excessive and expensive fluorinating re...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C07D241/44C07D213/64C07D213/84C07D239/34C07D333/64C07C31/38C07C29/00
CPCC07D213/64C07D213/84C07D239/34C07D241/44C07D277/68C07D471/04
Inventor 翁志强黄杨杰黄荣禄丁建平
Owner FUZHOU UNIV