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Synthesis method of high-purity o-bromoacetophnones

A synthesis method and technology of acetophenone, applied in the field of synthesis of high-purity o-bromoacetophenone, can solve the problems of expensive raw materials, lack of production conditions, low purity, etc., to achieve industrial production, improve production operation environment, shorten The effect of reaction time

Inactive Publication Date: 2016-04-27
SHANGHAI HUAXIAN NEW MATERIAL TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among them, most of the products of the Friedel-Crafts acylation method are para-products, and the yield is very low, which is not easy to purify; the raw materials of the 1-(2-bromophenyl)ethanol oxidation method are relatively expensive, and the steps are long, so the production conditions are not available ; O-bromoethylbenzene oxidation method often uses high temperature and high pressure and expensive catalysts, the oxidation is not complete, so that the raw material o-bromoethylbenzene is not easy to remove, and the purity is not high

Method used

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  • Synthesis method of high-purity o-bromoacetophnones

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preparation example Construction

[0016] The synthesis method of high-purity o-bromoacetophenone of the present invention comprises the following steps: add methylmagnesium bromide Grignard reagent in a container, under the normal temperature condition, drop the tetrahydrofuran solution of o-bromoxynil, after adding, there will be a large amount of A white solid appears; when there is no raw material detected by HPLC, stop the reaction; add it dropwise to hydrochloric acid solution, separate liquid, spin dry, and distill under reduced pressure to obtain a colorless liquid product (high-purity o-bromoacetophenone product). The molar ratio of o-bromoxynil and methylmagnesium bromide is 1:1.05.

[0017] The detailed steps of the present invention are as follows: Among them, the dosage is as follows: o-bromoxynil: 91g, methylmagnesium bromide (2M): 262.5ml, THF (Tetrahydrofuran, tetrahydrofuran): 90ml, concentrated hydrochloric acid: 60ml, toluene: 300ml. Add 262.5ml of methylmagnesium bromide (2M) into a 500ml re...

example 2

[0022] Example 2: The dosage is as follows: o-bromoxynil: 91g, methylmagnesium bromide (2M): 275ml, THF (Tetrahydrofuran, tetrahydrofuran): 90ml, concentrated hydrochloric acid: 70ml, toluene: 300ml.

[0023] Add 275ml (0.55) of methylmagnesium bromide (2M) into a 500ml reaction bottle, control the reaction temperature at 20-25°C, add dropwise 91g (0.5mol) o-bromoxynil and 90ml THF solution, control the reaction temperature at 20-25°C , The dropwise addition was completed in about 2 hours, and a large amount of white solid appeared after the addition. Reaction was continued at this temperature for 1 hour. Use HPLC to monitor the reaction situation, when the raw materials of the reaction solution disappear, stop the reaction, add the reaction solution dropwise to 70ml concentrated hydrochloric acid and 300ml water, separate the liquids, extract the aqueous phase with 300ml toluene, combine the organic phases, wash with 200ml water, and decompress -0.095MPa Concentrate until no...

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Abstract

The present invention discloses a synthesis method of a high-purity o-bromoacetophnones. The preparation method comprises the following steps: a methylmagnesium bromide Grignard reagent is added into a container, tetrahydrofuran and 2-Bromobenzonitrile are dropwise added into the container at room temperature, and then a lot of white solids appear; a reaction is stopped until no raw material is detected by HPLC spectrum; reaction solution is dropwise added into hydrochloric acid solution, and the hydrochloric acid solution treated reaction solution is subjected to skimming, spin drying and reduced pressure distillation processes, thereby obtaining colorless liquid products--high-purity o-bromoacetophnones. The preparation method improves the production and operation environment, can synthesize the high-purity o-bromoacetophnones under the condition of normal temperature, is easy to operate and control, shortens reaction time, reduces costs, and is beneficial to industrial production.

Description

technical field [0001] The invention relates to a synthesis method, in particular to a synthesis method of high-purity o-bromoacetophenone. Background technique [0002] O-bromoacetophenone is an important intermediate in organic synthesis, widely used in spices, medicine, pesticides, dyes, organic optoelectronics and other fields. At present, the preparation methods of o-bromoacetophenone mainly include: Friedel-Crafts acylation method, 1-(2-bromophenyl)ethanol oxidation method, and o-bromoethylbenzene oxidation method. Among them, most of the products of the Friedel-Crafts acylation method are para-products, the yield is very low, and it is not easy to purify; the raw materials of the 1-(2-bromophenyl)ethanol oxidation method are relatively expensive, and the steps are long, so the production conditions are not available The o-bromoethylbenzene oxidation method mostly uses high temperature and high pressure and expensive catalysts, and the oxidation is not complete, so th...

Claims

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Application Information

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IPC IPC(8): C07C49/807C07C45/44
Inventor 宋文志吴跃初郭磊
Owner SHANGHAI HUAXIAN NEW MATERIAL TECH CO LTD
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