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Synthesis method of 2-bromo-5-fluorobenzotrifluoride

A technology of fluorobenzotrifluoride and synthesis method, which is applied in chemical instruments and methods, preparation of nitro compounds, preparation of amino compounds, etc., can solve the problems of difficult handling and high price of m-fluorobenzotrifluoride, and achieve fewer types of impurities and higher product quality. The effect of stable quality and performance, cheap price

Active Publication Date: 2017-06-30
ZHEJIANG WEIHUA NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Patent Publication No. CN 104610015 reported that m-fluorobenzotrifluoride was used as raw material, sulfuric acid solution was used as solvent, bromic acid or bromate was used as bromination reagent to directly brominate the target compound, and the highest yield was 93.9%. The price of the raw material m-fluorobenzotrifluoride is high, and a large amount of waste acid is also produced in the bromination reaction of the benzene ring, and it is not easy to handle

Method used

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Experimental program
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Effect test

Embodiment 1

[0026] A kind of synthetic method of 2-bromo-5-fluorobenzotrifluoride, take o-trifluoromethylaniline as starting raw material, concrete steps comprise:

[0027] (1), Sandmeier bromination reaction

[0028] Slowly add 308 g (1.9 mol) of o-trifluoromethylaniline to 900 mL of hydrobromic acid (40%) under room temperature and stirring, and cool to 0°C with an ice bath after the addition is complete. Dissolve 135 g (1.95 mol) of sodium nitrite in 290 mL of water and add it dropwise to the reaction system with stirring, keeping the reaction temperature below 5°C. After the dropwise addition, continue to stir for 20 min and keep warm for later use. Add 28 g (0.34mol) of cuprous bromide and 80 mL of hydrobromic acid (40%) into a 2 L four-necked flask, stir vigorously at room temperature, pour the above diazo solution into the four-necked reaction flask, and the reaction is A large amount of gas was generated. After adding the diazo solution, continue to stir for 20 min, separate the...

Embodiment 2

[0036] (1), Sandmeier bromination reaction

[0037] Slowly add 308 g (1.9 mol) of o-trifluoromethylaniline to 970 mL of hydrobromic acid (40%) under room temperature and stirring, and cool to 0°C with an ice bath after the addition is complete. Dissolve 140 g (2.03 mol) of sodium nitrite in 325 mL of water, and slowly add it dropwise into the reaction system while stirring, and keep the reaction temperature below 5°C. After the dropwise addition, continue to stir for 20 min and keep warm for later use. Add 23.5 g (0.34 mol) of cuprous bromide and 65 mL of hydrobromic acid (40%) into a 2 L four-necked flask, stir vigorously at room temperature, pour the above-mentioned diazo solution into the four-necked reaction flask, and the reaction is A large amount of gas was generated. After adding the diazo solution, continue to stir for 20 min, separate the liquid, wash the lower organic phase with alkali until neutral, wash with water, and simply distill to obtain 386 g of yellow liq...

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Abstract

The invention relates to a synthesis method of 2-bromo-5-fluorobenzotrifluoride, belonging to the field of chemical synthesis. The method uses orthotrifluoromethyl aniline as the initial raw material, and comprises the following steps: (1) Sandmeyer bromination reaction; (2) nitration reaction; (3) catalytic hydrogenation reduction reaction; and (4) diazotization fluorination reaction. According to the method, the orthotrifluoromethyl aniline used as the raw material is subjected to Sandmeyer reaction bromination, nitration, hydrogenation reduction and diazotization fluorination to finally synthesize the 2-bromo-5-fluorobenzotrifluoride. The 2-bromo-5-fluorobenzotrifluoride product has the advantages of high purity (up to 99.0% or above), fewer impurity varieties and stable quality and properties.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a synthesis method of 2-bromo-5-fluorobenzotrifluoride. Background technique [0002] 2-Bromo-5-fluorotrifluorotoluene is a light yellow liquid, which is an important intermediate of medicine, pesticide and new liquid crystal material. For example, it is an important intermediate for the synthesis of antineoplastic drug bicalutamide, which is a An anti-androgen non-steroidal steroid with good tolerance and no obvious side effects after taking it. With the continuous expansion of the use of 2-bromo-5-fluorobenzotrifluoride, the market demand is also increasing. The synthesis method of 2-bromo-5-fluorobenzotrifluoride is seldom reported at home and abroad. Patent Publication No. CN102951996 reports that m-fluorobenzotrifluoride is used as raw material, through nitration, catalytic hydrogenation reduction, and finally by Sandmeyer reaction bromine The target compound was synthesi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C17/093C07C25/13
CPCC07C17/093C07C201/08C07C209/365C07C25/13C07C211/52C07C205/12C07C25/02
Inventor 陈静华吴江伟卜鲁周李俊奇常绚超张泉泉赵红英
Owner ZHEJIANG WEIHUA NEW MATERIAL CO LTD
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