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Preparation method of alpha-halogenated ketone compound

A halogenated ketone and compound technology, applied in the field of preparation of α-halogenated ketone compounds, can solve the problems of complex catalyst system structure, limited industrial use, environmental pollution and the like

Inactive Publication Date: 2021-09-14
DALIAN CHEMPHY CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the catalyst system is complex and expensive, difficult to recover and separate, difficult to recycle, and poor in economical practicability, which greatly limits its industrial use
[0006] Researchers have studied other reaction systems for synthesizing α-halogenated ketones, but they all need to use Cu(II), In(III), Hg(II) and other heavy metal ion complexes as catalysts, and these catalysts will cause severe Environmental pollution, and the post-processing of the product to remove metal ions is cumbersome, not suitable for large-scale industrial production

Method used

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  • Preparation method of alpha-halogenated ketone compound

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[0025] The present invention provides a kind of preparation method of α-halogenated ketone compound, comprises the following steps:

[0026] The terminal alkyne halide, organic solvent, acid and water are mixed and reacted to obtain α-halogenated ketone compounds.

[0027] In the present invention, the terminal alkyne halide has the structure shown in formula I:

[0028]

[0029] In formula I: R 1 is hydrocarbyl, substituted hydrocarbyl, hydrocarbyl formyl, aryl or substituted aryl, R 2 and R 3 are independently chain hydrocarbon groups, cyclohydrocarbyl groups or substituted hydrocarbon groups, and X is a halogen atom.

[0030] Specifically, when the R 1 When it is a hydrocarbon group, the hydrocarbon group is preferably an alkyl group, and the number of carbon atoms of the alkyl group is preferably 1 to 6, more preferably 2 to 4, and the alkyl group preferably includes chain alkyl and cycloalkyl, specifically preferably Methyl, ethyl, isopropyl or cyclohexyl; said R ...

Embodiment 1

[0044] The synthesis of embodiment 1 (4-chloro-2-methyl-butan-3-ketone-2-yl) benzene

[0045] Reaction formula:

[0046]

[0047] The amount of reaction raw materials is shown in Table 1:

[0048] Table 1 reaction raw material consumption

[0049] raw material molecular weight moles The molar ratio of quality (4-Chloro-2-methyl-but-3-yn-2-yl)benzene 178.66 1mol 1 178.66g 36.5% hydrochloric acid solution 36.5 5mol 5.0 500.00g Dichloroethane 98.97 10mol 10 989.7g

[0050] The reaction steps are as follows:

[0051] Dissolve 176.88 g of (4-chloro-2-methyl-but-3-yn-2-yl)benzene in 989.7 g of dichloroethane, add 500 g of 36.5% hydrochloric acid, raise the temperature to 66°C, and stir for 10 h , after all the raw materials have been converted, the reaction mixture is cooled to room temperature, washed with 2500 mL of aqueous sodium bicarbonate solution and 500 mL of brine, the organic phase is separated, the organic phase is ...

Embodiment 2

[0052] Embodiment 2: the synthesis of (4-chloro-2-methyl-butan-3-ketone-2-yl) benzene

[0053] Reaction formula:

[0054]

[0055] The amount of raw materials is shown in Table 2:

[0056] Table 2 reaction raw material consumption

[0057] raw material molecular weight moles The molar ratio of quality (4-Chloro-2-methyl-but-3-yn-2-yl)benzene 178.66 1mol 1 178.66g 36.5% hydrochloric acid solution 36.5 5mol 5.0 500.00g ethanol 46.07 10mol 10 460.7g

[0058] The preparation steps are as follows:

[0059] Dissolve 178.66 g of (4-chloro-2-methyl-but-3-yn-2-yl)benzene in 460.7 g of ethanol, add 500 g of 36.5% hydrochloric acid to it, raise the temperature to 78°C, stir and react for 10 h, and wait for the raw materials to After all conversions, the reaction mixture was cooled to room temperature, washed with 2500 mL of aqueous sodium bicarbonate solution and 500 mL of brine, separated the organic phase, concentrated under redu...

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Abstract

The invention relates to the technical field of pesticide chemistry, and provides a preparation method of an alpha-halogenated ketone compound. The preparation method comprises the steps: mixing terminal alkyne halide, an organic solvent, acid and water, and reacting to obtain the alpha-halogenated ketone compound. According to the preparation method provided by the invention, the terminal alkyne halide is directly reacted under the conditions of acid and water, and the use of a metal ion complex catalyst is avoided, so that the tedious operation of removing metal ions in the post-treatment process of the product is avoided, the whole process is simple and convenient to operate, green and environment-friendly, and the requirements of large-scale industrial production are met; and in addition, the method provided by the invention is high in raw material conversion rate, relatively high in product yield and purity, free of anhydrous and anaerobic operation and wide in substrate universality, and target molecules can be obtained from aliphatic, aromatic and other terminal alkyne halides at high yield. Furthermore, the preparation method provided by the invention is mild in reaction condition and easy to control.

Description

technical field [0001] The invention relates to the technical field of pesticide chemistry, in particular to a preparation method of α-halogenated ketone compounds. Background technique [0002] α-halogenated ketones are commonly used intermediates in organic synthesis, and are often used in fine organic synthesis fields such as pharmaceuticals, pesticides, and fine chemical intermediates, and have broad application space. Many organic fungicides and herbicides are realized through α-halogenated ketones as the main functional groups. [0003] At present, α-halogenated ketones are often synthesized by the reaction shown in formula A: [0004] [0005] In this reaction system, the Au complex is used as the catalyst, and the reaction yield is acceptable, and most of the substrates can reach more than 90%. However, the catalyst system is complex and expensive, difficult to recover and separate, difficult to recycle, and poor in economical practicability, which greatly limit...

Claims

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Application Information

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IPC IPC(8): C07C45/51C07C49/233C07C49/23C07C29/05C07C33/48C07C33/44C07C231/12C07C233/69C07C233/76
CPCC07C45/512C07C29/05C07C231/12C07C2601/14C07C33/483C07C49/233C07C33/44C07C49/23C07C233/69C07C233/76
Inventor 马晓爽王思宁阎述鹏蒲宏艺郭强徐海珍
Owner DALIAN CHEMPHY CHEM
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