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Synthesis method of 5-bromo-2-furaldehyde

A technology of furan formaldehyde and synthesis method, applied in the field of preparation of known compounds, can solve problems such as unfavorable sustainable development and economic development requirements, poor bromination reaction selectivity, serious environmental pollution, etc. Product yield and purity, the effect of reducing environmental pollution

Inactive Publication Date: 2012-02-15
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has poor bromination selectivity, produces a large number of different regioisomers, causes serious environmental pollution, and causes great corrosion to equipment. These shortcomings are not conducive to the sustainable development and economic development needs of large-scale industrial production.
In addition, there are few domestic research reports on the synthesis method of 5-bromo-2-furan aldehyde, and the main methods for producing 5-bromo-2-furan aldehyde are backward and cause great environmental pollution.

Method used

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  • Synthesis method of 5-bromo-2-furaldehyde
  • Synthesis method of 5-bromo-2-furaldehyde
  • Synthesis method of 5-bromo-2-furaldehyde

Examples

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Embodiment 1

[0027] In the present embodiment, 5-bromo-2-furancarbaldehyde is prepared according to the following steps:

[0028] (1) Preparation of Bromination Reagent

[0029] Put 12.3g of N-methylimidazole in a 500mL three-necked flask, and add 22.5g of n-bromobutane dropwise under stirring. The n-bromobutane has been distilled in advance to remove water. , heat up to the reaction system to generate reflux (105-140°C), keep the temperature for 9-10h, cool, and rotate to evaporate excess n-bromobutane for recovery, the reaction mixture is washed 3 times with ethyl acetate, each time with ethyl acetate The amount of ester was 40mL, and then dried in a vacuum oven at 60°C to constant weight to obtain a golden yellow viscous liquid, namely 1-butyl-3-methylimidazole bromide; the obtained 1-butyl bromide Base-3-methylimidazole was placed in a 500mL three-necked flask, and 4.8g of bromine was added dropwise with stirring at 10-15°C. The dropping time was controlled at 1h. After the drop was c...

Embodiment 2

[0033] In the present embodiment, 5-bromo-2-furancarbaldehyde is prepared according to the following steps:

[0034] (1) Preparation of Bromination Reagent

[0035] Put 12.3g of N-methylimidazole in a 500mL three-necked flask, and add 25.7g of brominated n-butane dropwise under stirring. The brominated n-butane has been distilled in advance to remove water. , heat up to the reaction system to generate reflux (105-140°C), keep the temperature for 9-10h, cool, and rotate to evaporate excess n-bromobutane for recovery, the reaction mixture is washed 3 times with ethyl acetate, each time with ethyl acetate The amount of ester was 40mL, and then dried in a vacuum oven at 70°C to constant weight to obtain a golden yellow viscous liquid, that is, 1-butyl-3-methylimidazole bromide; the obtained 1-butyl bromide Base-3-methylimidazole was placed in a 500mL three-necked flask, and 4.8g of bromine was added dropwise with stirring at 10-15°C. The dropping time was controlled at 1h. After ...

Embodiment 3

[0039] In the present embodiment, 5-bromo-2-furancarbaldehyde is prepared according to the following steps:

[0040] (1) Preparation of Bromination Reagent

[0041] Put 12.3g of N-methylimidazole in a 500mL three-necked flask, and add 25.7g of brominated n-butane dropwise under stirring. The brominated n-butane has been distilled in advance to remove water. , heat up to the reaction system to generate reflux (105-140°C), keep the temperature for 9-10h, cool, and rotate to evaporate excess n-bromobutane for recovery, the reaction mixture is washed 3 times with ethyl acetate, each time with ethyl acetate The amount of ester was 40mL, and then dried in a vacuum oven at 70°C to constant weight to obtain a golden yellow viscous liquid, that is, 1-butyl-3-methylimidazole bromide; the obtained 1-butyl bromide Base-3-methylimidazole was placed in a 500mL three-necked flask, stirred and added dropwise with 5.4g of bromine at 10-15°C, the dropping time was controlled at 1h, and reacted...

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Abstract

The invention discloses a synthesis method of 5-bromo-2-furaldehyde, which comprises the following steps: preparation of brominating agent: reacting N-methylimidazole and bromo-n-butane to generate bromo-1-butyl-3-methylimidazole, and reacting with bromine to obtain the brominating agent ionic liquid tribromo-1-butyl-3-methylimidazole; and bromination: adding furaldehyde into the prepared brominating agent to carry out bromination reaction, thereby generating the target product 5-bromo-2-furaldehyde. The invention avoids directly using the bromine, thereby enhancing the reaction cleanness of the industrial preparation and reducing the environmental pollution. The method disclosed by the invention enhances the product yield and purity. The yield is enhanced by nearly 9% as compared with the existing industrial traditional method; and in the method disclosed by the invention, the total yield is up to 87.6%, the product purity exceeds 96%, and other indexes are also enhanced correspondingly.

Description

1. Technical field [0001] The present invention relates to a process for the preparation of known compounds, in particular to the synthesis of 5-bromo-2-furfuraldehyde. 2. Background technology [0002] 5-bromo-2-furaldehyde (5-bromo-2-furaldehyde), also known as 5-bromofuraldehyde (5-bromofuraldehyde), 5-bromo-2-furfural (5-bromofuran-2-carboxaldehyde), is a Light yellow powder, melting point 80-85°C, boiling point 222.8°C / 760mmHg, flash point 112°C / 6mmHg, density ρ=1.748g / cm 3 , can be dissolved in carbon dichloride, carbon tetrachloride, ether and other organic solvents; its molecular formula is C 5 h 3 BrO 2 , and the relative molecular mass is 174.98. The structural formula of 5-bromo-2-furancarbaldehyde is as follows: [0003] [0004] Fufuraldehyde is an important basic chemical raw material, and there are more than 1,600 chemical products derived directly or indirectly from furfurylaldehyde. The furan formaldehyde bromide is an important deep-processing produ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/46
Inventor 彭新华戴志宏吴祥瑞荣媛
Owner HEFEI UNIV OF TECH
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