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Synthetic method of perfluoroalkane compound and derivative thereof

A synthesis method and technology of perfluoroalkane iodide, which is applied in the field of synthesis of perfluoroalkane compounds and their derivatives, can solve the problems of economy and environmental protection, and achieve mild reaction conditions, simple operation, and easy-to-obtain raw materials Effect

Pending Publication Date: 2022-05-13
UNIVERSITY OF CHINESE ACADEMY OF SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods use metals, expensive catalysts or excess alkali, which are insufficient in terms of economy and environmental protection.

Method used

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  • Synthetic method of perfluoroalkane compound and derivative thereof
  • Synthetic method of perfluoroalkane compound and derivative thereof
  • Synthetic method of perfluoroalkane compound and derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1, compound shown in synthetic formula II-1

[0034] according to figure 1 The compound shown in the synthetic route diagram synthetic formula II-1, concrete steps are as follows:

[0035] The pre-dried reaction tube was lowered to room temperature under vacuum, and the compound represented by formula VI (0.2 mmol) and perfluoroiodohexane represented by formula X (0.4 mmol) were added under the protection of nitrogen. After adding toluene (0.05 mL) and water (0.45 mL) to the mixture via syringe. Stir overnight (12h) at 60°C under a 50W blue LED (460nm) lamp. Then the reaction mixture is distilled under reduced pressure, separated by silica gel chromatography (the stationary phase of column chromatography: SiO 2 , mobile phase: petroleum ether, after collection, vacuum distillation obtains the product), to obtain the compound shown in formula II.

[0036]

[0037] The experimental data for structural verification are as follows:

[0038] Transparent oi...

Embodiment 2

[0040] Embodiment 2, compound shown in synthetic formula III-1

[0041] according to figure 1 The compound shown in the synthetic route diagram synthetic formula III-1, concrete steps are as follows:

[0042] The pre-dried reaction tube was reduced to room temperature under vacuum, and the compound represented by formula VII-1 (0.2 mmol) and perfluoroiodohexane represented by formula X (0.4 mmol) were added under nitrogen protection. After adding toluene (0.05 mL) and water (0.45 mL) to the mixture via syringe. Stir overnight (12h) at 60°C under a 50W blue LED (460nm) lamp. The reaction mixture was then subjected to silica gel chromatography (the stationary phase of column chromatography: SiO 2 , mobile phase: petroleum ether / ethyl acetate=5:1, the product was obtained by distillation under reduced pressure after collection), to obtain the desired compound of III-1.

[0043]

[0044] The experimental data for structural verification are as follows:

[0045] white solid...

Embodiment 3

[0047] Embodiment 3, compound shown in synthetic formula III-2

[0048] according to figure 1 The compound shown in the synthetic route diagram synthetic formula III-2, concrete steps are as follows:

[0049] The pre-dried reaction tube was lowered to room temperature under vacuum, and the compound represented by formula VII-2 (0.2 mmol) and perfluoroiodohexane represented by formula X (0.4 mmol) were added under nitrogen protection. After adding toluene (0.05 mL) and water (0.45 mL) to the mixture via syringe. Stir overnight (12h) at 60°C under a 50W blue LED (460nm) lamp. The reaction mixture was then subjected to silica gel chromatography (the stationary phase of column chromatography: SiO 2 , mobile phase: petroleum ether / ethyl acetate=5:1, the product was obtained by distillation under reduced pressure after collection), to obtain the desired compound of III-2.

[0050]

[0051] The experimental data for structural verification are as follows:

[0052] white solid...

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Abstract

The invention discloses a synthetic method of a perfluoroalkane compound and a derivative thereof. The method comprises the following steps: under the irradiation of blue light, by taking water and methylbenzene as solvents, carrying out free radical addition reaction on a compound shown as a formula V, a compound shown as a formula VI, a compound shown as a formula VII or a compound shown as a formula VIII and perfluoroalkyl iodide in an inert atmosphere, the compound shown in the formula I, the compound shown in the formula II, the compound shown in the formula III or the compound shown in the formula IV is obtained. According to the method disclosed by the invention, the perfluoroalkane compound and the derivative thereof are synthesized from water under the action of light without adding extra alkali or photocatalyst for the first time. Compared with the prior art, the synthetic method of the perfluoroalkane compound and the derivative thereof has the characteristics of easily available raw materials, simplicity in operation, mild reaction conditions, economy, greenness and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for synthesizing perfluoroalkane compounds and derivatives thereof. Background technique [0002] The introduction of perfluorinated structural units into organic molecules will significantly change their physical properties such as solubility and polarity; chemical properties and biological activities (Chem. Rev., 2015, 115, 765.). The introduction of fluorine structural units on the drug molecule can affect its drug activity, so that more candidate drugs will be produced in the market. With the update of fluorination methods and the continuous enrichment of commercial fluorinated intermediates, medicinal chemists have a wider range of choices in the way and strategy of introducing fluorine structural units into target molecules (J.Med.Chem.,2008, 51, 15, 4359–4369). Molecules containing perfluorinated structures have also been widely used in materials, such as insula...

Claims

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Application Information

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IPC IPC(8): C07B61/00C07D307/79C07D209/34C07C41/30C07C43/23C07C43/225C07C43/174C07C67/293C07C69/734C07C69/65C07C69/78C07C69/612C07C17/275C07C22/08C07C19/16C07D277/56C07D263/32
CPCC07B61/02C07D307/79C07D209/34C07C41/30C07C67/293C07C17/275C07D277/56C07D263/32C07C43/23C07C43/225C07C43/174C07C69/78C07C22/08C07C19/16C07C69/734C07C69/65C07C69/612Y02P20/55
Inventor 陈祥雨汪志祥方常振
Owner UNIVERSITY OF CHINESE ACADEMY OF SCIENCES
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