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Method for preparing 2, 6-difluoro-4-bromo-benzoyl chloride

A technology of bromobenzoyl chloride and difluorobromobenzene is applied in the field of preparation of 2,6-difluoro-4-bromobenzoyl chloride, and can solve the problems of high fluorine, high difficulty, difficult control and the like, and achieve product yield High, low production cost, good quality effect

Inactive Publication Date: 2016-08-17
BENGBU CHINA SYNCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Because fluorine itself is highly active, it is difficult to control in the reaction, especially when introducing molecules at specific positions, so the preparation of fluorine-containing organic compounds is still a very challenging research field

Method used

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  • Method for preparing 2, 6-difluoro-4-bromo-benzoyl chloride
  • Method for preparing 2, 6-difluoro-4-bromo-benzoyl chloride
  • Method for preparing 2, 6-difluoro-4-bromo-benzoyl chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] (1) In the reaction flask, add 0.65mol (1.3eq) diisopropylamine and 365ml THF, stir, cool down to -30°C, add 0.5mol (1.0eq) of n-butyllithium dropwise, and keep warm for the reaction after the dropwise addition. When the temperature is up, continue to cool down to -70.0°C, start to drop 0.5mol of raw material 3,5-difluorobromobenzene. Continue heat preservation reaction until the reaction of raw materials is complete, heat up and concentrate, add water, add hydrochloric acid dropwise for hydrolysis, adjust pH to 1-2, heat preservation reaction, when the reaction time is up, drain, beat and purify, and dry to obtain white solid 4-bromo-2, 0.37 mol of 6-difluorobenzoic acid, 0.48% moisture, 98.9% purity, and 74.0% yield.

[0019] (2) Put 0.68mol (2.0eq) of toluene into the reaction flask, 0.34mol of 4-bromo-2,6-difluorobenzoic acid prepared above, 0.4g of DMF, raise the temperature to 60.0°C, and start to add dropwise Sulfone 0.51mol (1.5eq), after dropwise addition, kee...

Embodiment 2

[0021] (1) In the reaction flask, add 0.65mol (1.3eq) diisopropylamine and 365ml THF, stir, cool down to -20°C, add 0.5mol (1.0eq) of n-butyllithium dropwise, and keep warm for the reaction after the dropwise addition. When the temperature is up, continue to cool down to -70.0°C, start to drop 0.5mol of raw material 3,5-difluorobromobenzene. Continue heat preservation reaction until the reaction of raw materials is complete, heat up and concentrate, add water, add hydrochloric acid dropwise for hydrolysis, adjust pH to 1-2, heat preservation reaction, when the reaction time is up, drain, beat and purify, and dry to obtain white solid 4-bromo-2, 0.32 mol of 6-difluorobenzoic acid, 0.52% moisture, 98.3% purity, and 64.0% yield.

[0022] (2) Put 0.96mol (3.0eq) of toluene into the reaction flask, 0.32mol of 4-bromo-2,6-difluorobenzoic acid prepared above, 0.4g of DMF, raise the temperature to 60.0°C, and start to drop chlorinated chlorinated Sulfone 0.51mol (1.5eq), after dropwi...

Embodiment 3

[0024] (1) In the reaction flask, add 1.0mol (2.0eq) diisopropylamine and 365ml THF, stir, cool down to -30°C, add 0.5mol (1.0eq) of n-butyllithium dropwise, and keep warm for the reaction after the dropwise addition. When the temperature is up, continue to cool down to -70.0°C, start to drop 0.5mol of raw material 3,5-difluorobromobenzene. Continue heat preservation reaction until the reaction of raw materials is complete, heat up and concentrate, add water, add hydrochloric acid dropwise for hydrolysis, adjust pH to 1-2, heat preservation reaction, when the reaction time is up, drain, beat and purify, and dry to obtain white solid 4-bromo-2, 0.34 mol of 6-difluorobenzoic acid, 0.36% moisture, 98.4% purity, and 68.0% yield.

[0025] (2) Put 1.02mol (3.0eq) of toluene into the reaction flask, 0.34mol of 4-bromo-2,6-difluorobenzoic acid prepared above, 0.4g of DMF, raise the temperature to 60.0°C, and start to drop chlorinated chlorinated Sulfone 0.68mol (2.0eq), after dropwis...

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Abstract

The invention discloses a preparation method of 2,6-difluoro-4-bromobenzoyl chloride, which relates to the technical field of organic synthesis. , thionyl chloride as a raw material, DMF as a catalyst, tetrahydrofuran and toluene as a solvent, 2,6-difluoro-4-bromobenzoyl chloride is prepared through steps such as organic lithiation, carboxylation, acyl chloride, and distillation. The raw materials used in the invention are easy to obtain, and the solvent toluene can be recycled and used mechanically during the reaction process, the production cost is low, the reaction conditions are mild, the aftertreatment is simple, the environmental pollution is small, the product yield is high, the quality is good, and it is suitable for industrial production.

Description

Technical field: [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 2,6-difluoro-4-bromobenzoyl chloride. Background technique: [0002] Fluorine-containing aromatic compounds are mainly used as intermediates of physiological compounds such as pesticides and medicines, and have good thermal stability and high fat solubility. For example, used as herbicides, fungicides, antineoplastic drugs, anti-Alzheimer's drugs, functional dyes and so on. Because fluorine itself is highly active, it is difficult to control in the reaction, especially when introducing molecules at specific positions, so the preparation of fluorine-containing organic compounds is still a very challenging research field. [0003] The compound 2,6-difluoro-4-bromobenzoyl chloride of the present invention is an intermediate with increasingly wide uses, and is a commonly used intermediate for synthesizing liquid crystal compounds, pharmaceutical co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/60C07C63/70
CPCC07C51/60C07C51/02C07C51/41C07F1/02
Inventor 杨青王松松赵士民徐剑霄
Owner BENGBU CHINA SYNCHEM TECH CO LTD
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