Method of synthesizing alpha-brominated ketone compound by hydrogen peroxide oxidizing and brominating method

An oxidative bromination method and a technology for ketone compounds, which are applied in the preparation of organic compounds, the preparation of carbon-based compounds, chemical instruments and methods, etc., can solve problems such as no further utilization of hydrogen bromide, and achieve low cost and convenient operation. , to avoid the effect of corrosion on the equipment

Inactive Publication Date: 2010-12-29
HEBEI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chinese patent CN1807382A discloses a method for preparing α-bromoketones by using bromine as a brominating agent and using water as a solvent to prepare α-bromoketones. Although water is used as a solvent, bromine is still used as a brominating agent, and the patent There is no further use of the hydrogen bromide produced
At the same time, the ketone compounds applicable in the technical solutions of the above two patents only include acetophenone and substituted acetophenone, while the bromination of other types of ketone compounds does not include

Method used

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  • Method of synthesizing alpha-brominated ketone compound by hydrogen peroxide oxidizing and brominating method
  • Method of synthesizing alpha-brominated ketone compound by hydrogen peroxide oxidizing and brominating method
  • Method of synthesizing alpha-brominated ketone compound by hydrogen peroxide oxidizing and brominating method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1. hydrogen bromide-hydrogen peroxide oxidative bromination method synthesizes brominated acetone

[0048]

[0049] Install a stirrer, a thermometer, a long reflux condenser and a feeding tube with a Y-shaped tube at the top of the four-necked flask. The two branches of the Y-shaped tube are each connected to a dropping funnel, and 29g (0.5 mol) acetone and 40mL water, respectively put into two dropping funnels 84.4g (0.5mol) 48% hydrobromic acid and 57g (0.5mol) 30% hydrogen peroxide solution, then add a few drops of hydrogen into the flask under stirring Bromic acid, then add a few drops of hydrogen peroxide dropwise, orange-red bromine will appear in the flask soon, slowly heat to 60-65°C, after the bromine completely fades, continue to drop hydrobromic acid, and then add hydrogen peroxide dropwise. Each time the reagent is repeatedly added dropwise, the bromine produced in the previous batch should basically fade, even if the color of the reactant rema...

Embodiment 2

[0050] Embodiment 2. Hydrogen bromide-hydrogen peroxide oxidative bromination method synthesizes 2-bromo-3-pentanone

[0051]

[0052] Install a stirrer, a thermometer, a long reflux condenser and a feeding tube with a Y-shaped tube at the top of the four-necked flask. The two branches of the Y-shaped tube are each connected to a dropping funnel. Add 43g (0.5 mol) 3-pentanone, 40mL water, 84.4g (0.5mol) 48% hydrobromic acid and 57g (0.5mol) 30% hydrogen peroxide solution are respectively charged in two dropping funnels, then add in the flask under stirring Add a few drops of hydrobromic acid, then drop a few drops of hydrogen peroxide, orange-red bromine will appear in the flask soon, heat slowly to 55-60°C, continue to drop hydrobromic acid after the bromine has completely faded, and then add dropwise hydrogen oxide. Each time the reagent is repeatedly added dropwise, the bromine produced in the previous batch should basically fade, even if the color of the reactant remai...

Embodiment 3

[0053] Embodiment 3. Hydrogen bromide-hydrogen peroxide oxidative bromination method synthesizes α-bromocyclohexanone

[0054]

[0055] Install a stirrer, a thermometer, a long reflux condenser and a feeding tube with a Y-shaped tube at the top of the four-necked flask. The two branches of the Y-shaped tube are each connected to a dropping funnel. Add 49g (0.5 mol) cyclohexanone, 40mL water, respectively load 84.4g (0.5mol) 48% hydrobromic acid and 57g (0.5mol) 30% hydrogen peroxide solution in two dropping funnels, then add several Drop hydrobromic acid, then add a few drops of hydrogen peroxide, orange-red bromine will appear soon in the flask, slowly heat to 50-60°C, continue to drop hydrobromic acid after the bromine has completely faded, and then add dropwise peroxide hydrogen. Each time the reagent is repeatedly added dropwise, the bromine produced in the previous batch should basically fade, even if the color of the reactant remains in an orange-yellow state. Repea...

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Abstract

The invention discloses a new process for synthesizing alpha-brominated ketone compound by a hydrogen peroxide oxidizing and brominating method and the process comprises a hydrogen bromide-hydrogen peroxide oxidizing and brominating method and a bromine-hydrogen peroxide oxidizing and brominating method. The process comprises the following specific steps of: when hydrogen bromide (solution of hydrobromic acid) is used as a bromination agent, mixing the ketone compound and the hydrobromic acid and directly dripping hydrogen peroxide into the mixture to oxidize the hydrogen bromide into bromine, and then performing a bromination reaction to generate alpha-brominated ketone; when the bromine is used as the bromination agent, brominating the ketone compound by using bromine liquid to generatethe alpha-brominated ketone compound and the hydrogen bromide; and after the bromine is completely reacted, oxidizing the hydrogen bromide generated in the reaction into the bromine by using the hydrogen peroxide, continuing to perform the bromination reaction on the bromine and the ketone until the ketone compound is completely reacted to generate the alpha-brominated ketone. In the invention, water is used as a solvent, the utilization rate of the bromine is nearly 100 percent, the final products of the reaction are only the alpha-brominated ketone and water; especially, when the hydrobromic acid is used as the bromination agent, the hydrobromic acid is nontoxic, tasteless and free of high corrosion of the bromine liquid without generating any harmful substance; and the process has the advantages of more convenient operation, high efficiency, energy conservation and environmental protection.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, in particular to a method for synthesizing α-bromoketones by the oxidative bromination method of hydrogen peroxide. Background technique [0002] α-Bromoketones are very important chemical intermediates for the synthesis of various medicines, pesticides, and dyes. With the continuous expansion of their application fields, people pay more and more attention to the research on their synthesis methods. Summarizing the research status at home and abroad, the focus of the research on the synthesis of α-bromoketones is two aspects: solvent and brominating agent. The earliest brominating agent was liquid bromine, and commonly used organic solvents include acetic acid, ether, dioxane, chloroform, dichloroethane, ethyl acetate, benzene, etc. Because liquid bromine is volatile and has a strong irritant and corrosive effect, it is unsafe to operate, seriously pollutes the environment and corrodes ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/63C07C49/16C07C49/463C07C49/457C07C49/80C07C49/84C07C49/813
Inventor 张书文李志云
Owner HEBEI UNIVERSITY
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