Preparation method of 2, 4, 6-trichlorophenyl substituted acetone

A technology of trichlorophenyl propyne and trichlorophenyl, which is applied in the field of preparation of 2,4,6-trichlorophenyl substituted acetone, can solve the problems of low reaction yield, environmental pollution, high price, etc. Achieve the effects of safe preparation method, obvious cost advantage, and favorable industrialization

Active Publication Date: 2021-06-22
江苏先导药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] 2,4,6-Trichlorophenyl substituted acetone is often used in the synthesis of medicines and pesticides, especially as an intermediate of the fungicide flufenapyramide, which has received much attention and research. There are mainly two synthetic methods reported in the literature. : The first one uses 2,4,6-trichlorobenzaldehyde as a raw material to obtain the target product through condensation with nitroethane and reduction of iron powder. The raw material price of 2,4,6-trichlorobenzaldehyde is high and the supply At th...

Method used

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  • Preparation method of 2, 4, 6-trichlorophenyl substituted acetone
  • Preparation method of 2, 4, 6-trichlorophenyl substituted acetone
  • Preparation method of 2, 4, 6-trichlorophenyl substituted acetone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] (Example 1) 2,4,6-trichlorophenyl substituted acetone

[0029]

[0030] Preparation of the target product in a small test:

[0031] In a 500ml four-neck flask equipped with a condenser, add 200mL dichloroethane, 0.2mol2,3,6-trichlorotoluene, 0.22molNBS in sequence under nitrogen protection, stir well and then slowly raise the temperature to 80°C, and then keep warm in the material The normalized content of 2,3,6-trichlorotoluene in liquid chromatography is 98% The target object 2,3,6-trichlorobenzyl bromide, the yield is 92%.

[0032] In a 500ml four-necked flask equipped with a condenser, add 200mLTHF, 0.2mol2,3,6-trichlorobenzyl bromide, 0.005mol anhydrous nickel chloride in sequence under nitrogen protection, stir well and cool down to 0°C, then dropwise add 0.21mol ethynylmagnesium bromide THF solution, after the dropwise addition, keep warm until the normalized content of 2,3,6-trichlorobenzyl bromide in the material is 95%, with a yield of 98%.

Embodiment 2

[0033] (Example 2) 2,4,6-trichlorophenyl substituted acetone

[0034]

[0035] Try to prepare the target product:

[0036] In a 3000L enamel kettle equipped with a graphite condenser, 1500L of dichloroethane, 390kg of 2,3,6-trichlorotoluene, and 390kg of NBS were sequentially pumped under nitrogen protection, stirred evenly, and slowly raised to 80°C, and then kept warm for 2 , 3,6-trichlorotoluene liquid chromatography normalized content98% Target 2,3,6-trichlorobenzyl bromide 490kg, yield 90%.

[0037] In a 5000l enamel kettle equipped with a graphite condenser, 1000LTHF, 540kg2,3,6-trichlorobenzyl bromide, 650g anhydrous nickel chloride were sequentially pumped under nitrogen protection, stirred evenly and cooled to 0°C, and then added dropwise 268kg of ethynylmagnesium bromide THF solution, after the dropwise addition, keep warm until the normalized content of 2,3,6-trichlorobenzyl bromide in the material is 96% of 2,4,6-trichlorophenylpropyne, with a yield of 90%.

...

Embodiment 3

[0039] (Example 3) 2,4,6-trichlorophenyl substituted acetone

[0040]

[0041] Preparation of the target product in a small test:

[0042] Partial results of the optimization of the first-step halogenation parallel reaction for halogenation reagents are as follows:

[0043] serial number Halogenating reagent solvent yield 1 Thionyl chloride chlorobenzene 54％ 2 NCS Dichloroethane 83％ 3 Chlorine Chloroform 88％ 4 Bromine benzene 90％

[0044] Partial results of parallel optimization of the second-step coupling reaction for metal catalysts are as follows:

[0045] serial number catalyst yield 1 Ferrous chloride 92％ 2 Cuprous bromide 53％ 3 Triphenylphosphine nickel chloride 95％ 4 nickel sulfate 88％

[0046] The results of the parallel optimization of the third step water addition reaction on the acid catalyst are as follows:

[0047] serial number acid solvent yield...

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Abstract

The invention relates to a preparation method of 2, 4, 6-trichlorophenyl substituted acetone, which comprises the following steps: adding 2, 4, 6-trichlorotoluene and a chlorination reagent into an organic solvent at a certain temperature to prepare 2, 4, 6-trichlorophenyl benzyl chloride, then coupling with ethynyl magnesium halide under the action of a metal catalyst, and then carrying out acid catalysis and water addition to finally obtain the product 2, 4, 6-trichlorophenyl substituted acetone. The method provided by the invention has the advantages of many raw material sources, obvious cost advantage, safer and more convenient preparation method, high total yield and less three wastes, and is beneficial to industrialization.

Description

technical field [0001] The invention relates to a preparation method of 2,4,6-trichlorophenyl substituted acetone, in particular to a method for preparing 2,4,6-trichlorotoluene through halogenation, metal-catalyzed Grignard reagent coupling, and acid-catalyzed alkyne water addition. A method for the preparation of 2,4,6-trichlorophenyl substituted acetone. Background technique [0002] 2,4,6-Trichlorophenyl substituted acetone is often used in the synthesis of medicines and pesticides, especially as an intermediate of the fungicide flufenapyramide, which has received much attention and research. There are mainly two synthetic methods reported in the literature. : The first one uses 2,4,6-trichlorobenzaldehyde as a raw material to obtain the target product through condensation with nitroethane and reduction of iron powder. The raw material price of 2,4,6-trichlorobenzaldehyde is high and the supply At the same time, a large amount of iron sludge is produced during the reduc...

Claims

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Application Information

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IPC IPC(8): C07C45/26C07C49/233C07C17/14C07C25/02C07C17/263C07C25/10
CPCC07C45/26C07C17/14C07C17/2632C07C49/233C07C25/02C07C25/10
Inventor 陈月霞肖石基
Owner 江苏先导药业有限公司
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