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Synthetic method of insecticide spirotetramat intermediate 2,5-dimethylphenylacetyl chloride

A technology of dimethylphenylacetyl and spirotetramat, which is applied in the fields of chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as environmental pollution, emission of harmful substances, poisonous and harmful to human body, etc. High efficiency, less pollution discharge, less side effects

Active Publication Date: 2020-02-18
SHANDONG ACADEMY OF PESTICIDE SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These chlorinated reagents are often highly irritating, toxic and harmful to the human body, unsafe to use, and very unfavorable for production operations; the use of these halogenated reagents is likely to produce harmful emissions and environmental pollution
Simultaneously, above-mentioned three kinds of synthetic methods that obtain 2,5-dimethylphenylacetyl chloride, respective total yields are also not ideal
These all limit the development of 2,5-dimethylphenylacetyl chloride industry

Method used

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  • Synthetic method of insecticide spirotetramat intermediate 2,5-dimethylphenylacetyl chloride
  • Synthetic method of insecticide spirotetramat intermediate 2,5-dimethylphenylacetyl chloride

Examples

Experimental program
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Effect test

Embodiment 1

[0029] The synthetic method of 2,5-dimethylphenylacetyl chloride comprises the following steps:

[0030] 1) Add 1mol of 2-bromo-p-xylene, chloroacetyl chloride, catalyst and DMSO into the reaction kettle, heat up to 100°C under stirring, react for 5h, then add the mixture of sodium sulfite and water dropwise, and control the dropping time After the dropwise addition, the reaction temperature was increased to 135°C, and the reaction was continued for 7.5 hours to complete;

[0031] The amount ratio of 2-bromo-p-xylene and chloroacetyl chloride is a molar ratio of 1:1.14, the amount ratio of 2-bromo-p-xylene and catalyst is a mass ratio of 1:0.07, 2-bromo-p-xylene and DMSO The consumption ratio of 1g:13ml, the consumption ratio of 2-bromo p-xylene and sodium sulfite is 1:1.18 in molar ratio, and the consumption ratio of sodium sulfite and water is 1:4.5 in mass ratio.

[0032] The preparation process of the catalyst is as follows: mix ruthenium oxide and 10% palladium carbon ac...

Embodiment 2

[0035] The synthetic method of 2,5-dimethylphenylacetyl chloride comprises the following steps:

[0036] 1) Add 1mol of 2-iodo-p-xylene, bromoacetyl chloride, catalyst and DMF to the reaction kettle, raise the temperature to 90°C under stirring, react for 3h, then add the mixture of sulfite and water dropwise, and control the dropwise The addition time is 30min, after the dropwise addition, the reaction temperature is raised to 120°C, and the reaction is continued for 6h to end;

[0037] The consumption ratio of 2-bromo-p-xylene and chloroacetyl chloride is molar ratio 1:1.05, the consumption ratio of 2-bromo-p-xylene and catalyst is mass ratio 1:0.05, 2-bromo-p-xylene and DMF The dosage ratio is 1g:13ml, the consumption ratio of 2-bromo-p-xylene and potassium sulfite is 1:1.18 in molar ratio, and the consumption ratio of potassium sulfite and water is 1:4.5 in mass ratio.

[0038] The preparation process of the catalyst is as follows: mix ruthenium oxide and 5% palladium car...

Embodiment 3

[0041] The synthetic method of 2,5-dimethylphenylacetyl chloride comprises the following steps:

[0042] 1) Add 1 mol of 2-chloro-p-xylene, chloroacetyl chloride, catalyst and DMSO to the reaction kettle, raise the temperature to 120°C under stirring, react for 6 hours, then add the mixture of sodium sulfite and water dropwise, and control the dropping time 55min, after the dropwise addition, raise the reaction temperature to 145°C, and continue the reaction for 8h to end;

[0043] The consumption ratio of 2-bromo-p-xylene and chloroacetyl chloride is molar ratio 1:1.16, the consumption ratio of 2-bromo-p-xylene and catalyst is mass ratio 1:0.09, 2-bromo-p-xylene and DMF The consumption ratio of 1g:15ml, the consumption ratio of 2-bromo p-xylene and sodium sulfite is 1:1.21 in molar ratio, and the consumption ratio of sodium sulfite and water is 1:5 in mass ratio.

[0044] The preparation process of the catalyst is as follows: mix ruthenium oxide and 10% palladium carbon acco...

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Abstract

The invention discloses a synthetic method of an insecticide spirotetramat intermediate 2,5-dimethyl phenylacetyl chloride, belonging to the field of pesticide pharmacy. The synthetic method is characterized by comprising the step of reacting 2-halogenated p-xylene with halogenated acetylchloride in the presence of a catalyst, so as to obtain 2,5-dimethyl phenylacetyl chloride. The reaction process comprises the following steps: (1) adding 2-halogenated p-xylene, halogenated acetylchloride, the catalyst and a solvent A into a reaction kettle, heating to 90-120 DEG C while stirring, reacting for 3-6 hours, dropwise adding a mixture of sulfate and water for 30-55 minutes, after the dropwise adding is finished, heating to 120-145 DEG C, and continuing to react for 6-8 hours; and (2) cooling the system, filtering to remove insoluble substances so as to obtain a filtrate, adding the filtrate into water which is 4-6 times of volume of the filtrate, adding a solvent B which is 4-6 times of volume of the filtrate, standing for layering, washing with an organic phase, drying by virtue of a drying agent, and concentrating, so as to obtain 2,5-dimethyl phenylacetyl chloride. The synthetic method has the beneficial effects that the steps are few, the yield is relatively high, and the pollution discharge amount is relatively low.

Description

technical field [0001] The invention belongs to the field of pesticide pharmacy, and in particular relates to a method for synthesizing an insecticide spirotetramat intermediate 2,5-dimethylphenylacetyl chloride. Background technique [0002] Spirotetramat common name spirotetramat, chemical name cis-3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]-decane 3- Alkenyl 4-yltoluene, discovered by Bayer in the process of screening herbicides, is a new type of tetronic acid insecticide, and it is also the only insecticide with two-way systemic conductivity so far. This unique systemic property protects young stems, leaves and roots from the growth of pest eggs and larvae. Another feature is its long-lasting effect, which can provide effective control for up to 8 weeks. [0003] 2,5-Dimethylphenylacetyl chloride is an important intermediate for the synthesis of flonicamid. In the prior art, the synthetic method of this intermediate is summed up and has three kinds: [000...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C51/62C07C57/30
CPCC07C51/62C07C57/30
Inventor 付洪信杨朝晖王玲
Owner SHANDONG ACADEMY OF PESTICIDE SCI