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A method of preparing 2,4,6-trifluorobenzaldehyde

A technology of trifluorobenzaldehyde and trifluorobenzene, which is applied in the field of compound preparation, achieves the effects of high yield, easy availability of raw materials, and reduced production costs

Active Publication Date: 2017-08-15
SHANGYU HUALUN CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This synthetic method has high purity and yield, but the disadvantage is that the dichloromethyl ether method in the fluorobenzoylation method usually needs to separate the ortho isomers

Method used

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  • A method of preparing 2,4,6-trifluorobenzaldehyde

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] (1) Add 2000mL tetrahydrofuran and 320g diisopropylamine into the reaction flask, cool the system to -50°C with liquid nitrogen, stir under nitrogen protection, add dropwise 1240mL n-butyllithium (concentration is 2.5mol / L, the same below ), control the temperature not to exceed -10°C, and after the dropwise addition is completed, a tetrahydrofuran solution of lithium diisopropylamide is obtained, which is kept at a temperature below -10°C for use.

[0031] (2) Take another reaction bottle, add 3000mL tetrahydrofuran and 396g 1,3,5-trifluorobenzene, cool the system to -80°C with liquid nitrogen, and drop the standby lithium diisopropylamide under the protection of nitrogen The tetrahydrofuran solution, the temperature is controlled not to exceed -75 ° C, after the dropwise addition is completed, the reaction is kept for 3 hours.

[0032] (3) Add 225 g of dimethylformamide dropwise to the reaction solution, control the temperature not to exceed -75° C., and keep the reac...

Embodiment 2

[0036] (1) Add 1800mL tetrahydrofuran and 310g diisopropylamine into the reaction flask, cool the system to -50°C with liquid nitrogen, stir under nitrogen protection, add 1240mL n-butyllithium dropwise, control the temperature not to exceed -10°C, drop After the addition is complete, a tetrahydrofuran solution of lithium diisopropylamide is obtained, which is kept at -10°C until use.

[0037] (2) Take another reaction bottle, add 3000mL tetrahydrofuran and 400g 1,3,5-trifluorobenzene, cool the system to -80°C with liquid nitrogen, and drop the ready-to-use lithium diisopropylamide under the protection of nitrogen The tetrahydrofuran solution, the temperature is controlled not to exceed -75°C, and the reaction is kept for 4 hours after the dropwise addition is completed.

[0038] (3) Add 225 g of dimethylformamide dropwise to the reaction solution, control the temperature not to exceed -75° C., and keep the reaction for 1 hour after the dropwise addition is completed.

[0039...

Embodiment 3

[0042] (1) Add 1800mL tetrahydrofuran and 310g diisopropylamine into the reaction flask, cool the system to -55°C with liquid nitrogen, stir under nitrogen protection, add 1240mL n-butyllithium dropwise, control the temperature not to exceed -10°C, drop After the addition is complete, a tetrahydrofuran solution of lithium diisopropylamide is obtained, which is kept at -10°C until use.

[0043] (2) Take another reaction bottle, add 2500mL tetrahydrofuran and 400g 1,3,5-trifluorobenzene, cool the system to -80°C with liquid nitrogen, and drop the standby lithium diisopropylamide under the protection of nitrogen The tetrahydrofuran solution, the temperature is controlled not to exceed -75 ° C, and the temperature is kept for 5 hours after the dropwise addition is completed.

[0044] (3) Add 228 g of dimethylformamide dropwise to the reaction solution, control the temperature not to exceed -75° C., and keep the reaction for 1 hour after the dropwise addition is completed.

[0045...

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Abstract

A method of preparing 2,4,6-trifluorobenzaldehyde is provided. The method includes (1) preparing a tetrahydrofuran solution of lithium diisopropylamide, and keeping the solution for later use; (2) cooling to a temperature ranging from -85 DEG C to -80 DEG C, adding dropwise the tetrahydrofuran solution of the lithium diisopropylamide into a tetrahydrofuran solution of 1,3,5-trifluorobenzene under nitrogen protection, and reacting at a maintained temperature for 3-5 h after the addition is finished; (3) adding dropwise dimethylformamide into the reaction solution, and maintaining the temperature at a temperature ranging from -80 DEG C to -75 DEG C for 50-70 min; (4) maintaining the temperature to be -5-0 DEG C, adding dropwise glacial acetic acid, water and diluted hydrochloric acid in order into the reaction solution, adjusting the pH to be 1-2, and stirring the solution for 10-20 min after addition is finished to obtain a crude product; and (5) subjecting the crude product to after-treatment to obtain a target product that is the 2,4,6-trifluorobenzaldehyde. The lithium diisopropylamide that is a non-nucleophilic organic base is applied, thus providing a novel route for preparing the 2,4,6-trifluorobenzaldehyde.

Description

technical field [0001] The invention belongs to the field of compound preparation, in particular to a preparation method of 2,4,6-trifluorobenzaldehyde. Background technique [0002] In the chemical and pharmaceutical field, due to the introduction of fluorine atoms, most fluorine-containing organic compounds have specific properties that cannot be compared with other organic compounds. The unique and excellent properties of fluorine-containing organic compounds have aroused great interest in it. In recent years, fluorine-containing intermediates have been studied by more and more scholars due to their excellent pharmacological and physiological activities. Fluorobenzaldehyde is an important class of organic chemical raw materials and intermediates, which can be widely used in pesticides, medicines, Synthesis of dyes and resins. However, due to the relatively backward synthesis technology, there is a large gap between supply and demand. Therefore, the development of its ne...

Claims

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Application Information

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IPC IPC(8): C07C45/45C07C47/55
CPCC07C45/455C07F1/02C07C47/55
Inventor 李典正赵大文黄光亮
Owner SHANGYU HUALUN CHEM
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