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A kind of hydrodehalogenation method of halogenated aromatic hydrocarbon

A halogenated aromatic hydrocarbon, hydrodehalogenation technology, applied in the field of hydrodehalogenation of halogenated aromatic hydrocarbons, can solve the problems of high bond energy, difficult catalysis, low applicability, etc., achieves low toxicity, easy realization, and increased yield Effect

Active Publication Date: 2021-05-11
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But its disadvantage is that its applicability is relatively low compared with transition metal catalysis
[0006] Catalytic hydrogenation of palladium carbon and metal nickel is a recognized method of hydrodehalogenation, but such methods inevitably use hydrogen and pressure reactors
Moreover, due to the high bond energy of the C-F bond and the C-Cl bond, it is difficult for this type of metal catalyst to catalyze it.

Method used

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  • A kind of hydrodehalogenation method of halogenated aromatic hydrocarbon
  • A kind of hydrodehalogenation method of halogenated aromatic hydrocarbon
  • A kind of hydrodehalogenation method of halogenated aromatic hydrocarbon

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The hydrodechlorination of embodiment 1 o-chlorobenzoic acid

[0032] Step 1: Weigh 78mg (0.5mmol%) of o-chlorobenzoic acid, 34mg (0.5mmol) of imidazole, 24mg (12mmol%) of cupric ammonium sulfate (hexahydrate), 11mg (2mmol%) of rose bengal, lithium tert-butoxide t- BuOli 72mg (0.9mmol) in a quartz reaction tube. Add 1.5 ml each of isopropanol and DMF as solvent.

[0033] Step 2: Place the quartz reaction tube under 254nm ultraviolet light for 72 hours under air condition. The reaction formula is as follows:

[0034]

[0035] Step 3: After the reaction was completed, the product was separated by column chromatography, and the yield was 87%. The resulting product is benzoic acid.

Embodiment 2

[0036] Example 2 Hydrodechlorination of 2-chloro-nitrogen-phenylbenzamide

[0037] Step 1: Weigh 116mg (0.5mmol) of 2-chloro-nitrogen-phenylbenzamide, 34mg (0.5mmol) of imidazole, 24mg (12mmol%) of copper ammonium sulfate (hexahydrate), and 11mg (2mmol%) of rose bengal , Lithium tert-butoxide t-BuOli 72mg (0.9mmol) in a quartz reaction tube. Add 1.5 ml each of isopropanol and DMF as solvent.

[0038] Step 2: Place the quartz reaction tube under 254nm ultraviolet light for 72 hours under air condition. The reaction formula is as follows:

[0039]

[0040] Step 3: After the reaction was completed, the product was separated by column chromatography, and the yield was 87%. The resulting product is nitrogen-phenylbenzamide.

Embodiment 3

[0041] Example 3 The hydrodechlorination of 2-chloro-4-methylbenzoic acid

[0042] Step 1: Weigh 85mg (0.5mmol) of 2-chloro-4-methylbenzoic acid, 34mg (0.5mmol) of imidazole, 24mg (12mmol%) of cupric ammonium sulfate (hexahydrate), 11mg (2mmol%) of rose bengal, Lithium tert-butoxide t-BuOli 72mg (0.9mmol) in a quartz reaction tube. Add 1.5 ml each of isopropanol and DMF as solvent.

[0043] Step 2: Place the quartz reaction tube under 254nm ultraviolet light for 72 hours under air condition. The reaction formula is as follows:

[0044]

[0045] Step 3: After the reaction was completed, the product was separated by column chromatography, and the yield was 85%. The resulting product is p-toluic acid.

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Abstract

The invention relates to a dehalogenation reaction, in particular to a method for hydrogenation dehalogenation of halogenated aromatic hydrocarbons. The method uses imidazole or imidazole derivatives or analogues as a reducing agent to hydrogenate and dehalogenate halogenated aromatic hydrocarbons into aromatic hydrocarbons under the action of light and photosensitizers. The specific operation is as follows: dissolving halogenated aromatic hydrocarbon, imidazole or imidazole derivatives or analogs, catalyst, photosensitizer and basic compound in organic solvent, and then reacting in the light source environment under air conditions, and finally using column chromatography The product was separated by the method, and the yield could reach 89%. In the present invention, imidazole or imidazole derivatives or analogues are used as reducing agents for hydrogenation dehalogenation for the first time, and photosensitizers are used for hydrogenation dehalogenation reactions for the first time. A mild and easy-to-manipulate new method is provided for the hydrodehalogenation of halogenated aromatic hydrocarbons.

Description

technical field [0001] The invention relates to a dehalogenation reaction, in particular to a method for hydrogenation dehalogenation of halogenated aromatic hydrocarbons. Background technique [0002] Among halogenated arenes, the carbon-halogen bond energy of brominated arenes and iodo arenes is small, while the bond energy of chlorinated arenes and fluorinated arenes is relatively large; and brominated arenes and iodoarenes are easy to prepare and relatively cheap, while chlorinated arenes And fluorinated aromatics are generally more expensive, so chlorinated aromatics and fluorinated aromatics have good application value after effective treatment; and most of the toxic halogenated aromatics reported so far are chlorinated aromatics, such as HHC, Dioxin etc. [0003] There have been many reports on the hydrogenation of aryl and alkyl halides. Metal catalysts have shown excellent performance in this respect. But the activation of C-F bonds and C-Cl bonds by transition m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C51/377C07C201/12C07C231/12C07C63/06C07C233/65C07C63/04C07C205/57
CPCC07C51/377C07C201/12C07C231/12C07C63/06C07C233/65C07C63/04C07C205/57
Inventor 房晓敏王帅印许静徐浩丁涛王槟鑫韩乃娟张文凯徐元清刘保英王延鹏任艳蓉
Owner HENAN UNIVERSITY
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