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Preparation methods of 4-bromo-2,6-difluoro-trifluorotoluene and intermediate thereof

A technology of difluorobenzotrifluoride and difluorobenzotrifluoride, which is applied in the field of preparation of 4-bromo-2,6-difluorobenzotrifluoride and its intermediates, can solve the problems of unsuitability for industrialized production, serious environmental pollution, Harsh reaction conditions and other problems, to achieve the effect of easy industrial production, high reaction conversion rate, and mild reaction conditions

Active Publication Date: 2013-04-24
LIANHE CHEM TECH +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] The technical problem to be solved by the present invention is to overcome the cumbersome process, harsh reaction conditions, high equipment requirements, serious corrosion, serious environmental pollution and high cost in the existing preparation method of 4-bromo-2,6-difluorobenzotrifluoride , not suitable for defects such as industrialized production, but provides a preparation method of 4-bromo-2,6-difluorobenzotrifluoride and its intermediate 2,6-difluoro-4-bromotrichloromethylbenzene

Method used

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  • Preparation methods of 4-bromo-2,6-difluoro-trifluorotoluene and intermediate thereof
  • Preparation methods of 4-bromo-2,6-difluoro-trifluorotoluene and intermediate thereof
  • Preparation methods of 4-bromo-2,6-difluoro-trifluorotoluene and intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Example 1 Preparation of 4-bromo-2,6-difluorobenzotrifluoride

[0056] Step (1) Preparation of 4-bromo-2,6-difluorobenzotrichloride

[0057] 500mL four-necked bottle, install a thermometer, mechanical stirring, condenser, tail gas absorption device, under the protection of nitrogen, add 118.5g (0.5mol) 4-bromo-2,6-difluorobenzoic acid, 250.2g (1.2mol) Phosphorus chloride, 146.2g (0.75mol) phenylphosphonyl dichloride, after the addition is complete, the temperature is raised to 90~105°C, and the temperature of the reaction system is kept at 90~105°C for 9 hours. GC detects that the reaction of the raw materials is complete, and the temperature of the reaction bottle is lowered. Refit the device to vacuum distillation, distill out the by-product phosphorus oxychloride, cool down to room temperature, pour the oily residue into 5% aqueous solution of sodium bicarbonate, adjust the pH of the system to 7~8, add n-hexane for extraction, and separate layers , the aqueous layer...

Embodiment 2

[0063] Example 2 Preparation of 4-bromo-2,6-difluorobenzotrifluoride

[0064] Step (1) Preparation of 4-bromo-2,6-difluorobenzotrichloride

[0065] 500ml four-necked bottle, install a thermometer, mechanical stirring, condenser, tail gas absorption device, under the protection of nitrogen, add 118.5g (0.5mol) 4-bromo-2,6-difluorobenzoic acid, 312.7g (1.5mol) five Phosphorus chloride, 195g (1mol) phenylphosphonyl dichloride, after the addition is complete, heat up to 90~105°C, keep the temperature of the reaction system between 90~105°C for 15 hours, check that the reaction of the raw materials is complete, cool down the reaction bottle, and refit the device For vacuum distillation, distill out the by-product phosphorus oxychloride, cool down to room temperature, pour the oily residue into 5% aqueous solution of sodium bicarbonate, adjust the system pH=7~8, add n-hexane for extraction, separate layers, and water layer Back-extracted once, combined the organic layers, passed th...

Embodiment 3

[0068] Example 3 Preparation of 4-bromo-2,6-difluorobenzotrifluoride

[0069] Step (1) Preparation of 4-bromo-2,6-difluorobenzotrichloride

[0070] 500mL four-necked bottle, install a thermometer, mechanical stirring, condenser, tail gas absorption device, under the protection of nitrogen, add 118.5g (0.5mol) 4-bromo-2,6-difluorobenzoic acid, 250.2g (1.2mol) Phosphorous chloride, 146.2g (0.75mol) phenylphosphine dichloride, after the addition is completed, the temperature is raised to 90~105°C, and the temperature of the reaction system is kept at 90~105°C for 9 hours. The device is converted to vacuum distillation, the by-product phosphorus oxychloride is distilled off, the temperature is lowered to room temperature, the oily residue is poured into 5% sodium bicarbonate aqueous solution, the pH of the system is adjusted to 7~8, n-hexane is added for extraction, and the layers are separated. The aqueous layer was back-extracted once, the organic layers were combined, passed t...

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Abstract

The invention discloses preparation methods of 4-bromo-2,6-difluoro-trifluorotoluene and an intermediate thereof. The intermediate of the 4-bromo-2,6-difluoro-trifluorotoluene is 4-bromo-2,6-difluoro-trichlorotoluene. The preparation method of 4-bromo-2,6-difluoro-trichlorotoluene comprises the following steps: reacting 4-bromo-2,6-difluoro-phenylformic acid with arylphosphonic tetrachloro expressed by formula 1 as follows; the structural formula of the arylphosphonic tetrachloro is expressed by formula 1, and the structural formula of aryl group in the arylphosphonic tetrachloro is expressed by formula 2, wherein R1, R2, R3, R4 and R5 are respectively independently hydrogen, C1-4 alkyl, F, Cl, Br or I. The preparation method is relatively low in cost, simple in technology, mild in reaction condition, high in rate of conversion, simple in post-processing operation, relatively high in product yield and relatively good in purity, thereby preventing toxic gas reactive materials of methyl iodide and the like, and reducing the requirement of the device. The preparation method is safe and efficient, and is easy for industrial production.

Description

technical field [0001] The invention specifically relates to a preparation method of 4-bromo-2,6-difluorobenzotrifluoride and its intermediate. Background technique [0002] Fluorine-containing aromatic compounds are mainly used as active intermediates of pesticides and medicines, and have good thermal stability, such as herbicides, fungicides, anticancer drugs, anti-senile dementia drugs, and dyes. Because the activity of fluorine atoms is relatively high, it is difficult to control in the reaction, especially the introduction at a specific position is even more difficult, so the preparation of fluorine-containing organic compounds is still a very challenging research direction. [0003] The compound 4-bromo-2,6-difluorobenzotrifluoride described in the present invention is widely used as an intermediate of liquid crystal, pharmaceutical and pesticide compounds. [0004] The most commonly used methods for introducing trifluoromethyl into aromatic rings are: [0005] 1. Ch...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C25/13C07C17/093C07C17/20
Inventor 王萍樊小彬彭寅生郭章红李强江朋
Owner LIANHE CHEM TECH
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