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Preparation method of 7-bromobenzofuran

A technology of furan and bromobenzene, which is applied in the field of preparation of 7-bromobenzofuran, can solve the problems of expensive reagents, high cost, and limited substrates, and achieve the effects of easy industrial scale-up, reduced production costs, and avoiding pollution

Active Publication Date: 2014-04-16
SHANDONG YOUBANG BIOCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional methods have played an important role in the synthesis of biologically active benzofurans, but there are generally problems such as long routes, harsh substrate and reaction conditions, and limited expansion of substituted functional groups.
Palladium and other precious metals are used as catalysts to synthesize benzofuran, which can overcome the shortcomings of traditional synthetic methods, and the yield has been further improved, but the cost is higher
In recent years, the cheap transition metal copper has gradually become a new hotspot of people's research. The research on using copper as a catalyst to synthesize benzofuran has achieved relatively gratifying results, but there are still limitations in substrates and expensive reagents, etc. shortcoming
Although these achievements are very successful, their industrial production has encountered great challenges, and the heavy metal catalysts used will cause pollution to the environment

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019]

[0020] Add 1,4-dioxane (800 mL) into a 2000 mL three-necked round bottom flask, then add o-bromophenol (210 g, 1.213 mol), potassium carbonate (750 g, 5.426 mol) and 2- Bromoacetaldehyde dimethyl acetal (300 g, 1.775 mol). Stirring was started and heated to reflux for 22 hours. TLC and GC followed the reaction. After the reaction was complete, most of the 1,4-dioxane was distilled off. Add 600 mL each of water and ethyl acetate to the residue, stir the mixture for 40 minutes, and separate the organic phase. The aqueous phase was extracted with 200 mL of ethyl acetate, and the combined organic phases were dried overnight with sodium sulfate. The obtained crude product (305 g) was directly used in the next reaction.

[0021] Add chlorobenzene (1000 mL) to a 5000 mL three-necked round-bottomed flask, then add the above crude product 1-bromo-2'-(2,2-dimethoxyethyl)benzene (305 g), phosphoric acid (750g). Stirring was started and heated to reflux for 27 hours. TL...

Embodiment 2

[0023] Add N,N-dimethylformamide (800 mL) into a 2000 mL three-necked round bottom flask, then add o-bromophenol (210 g, 1.213 mol), potassium carbonate (750 g, 5.426 mol) and 2 -Bromoacetaldehyde dimethyl acetal (300 g, 1.775 mol). Stirring was started and heated to reflux for 26 hours. TLC and GC followed the reaction. After the reaction was completed, most of the N,N-dimethylformamide was distilled off. Add 800 mL each of water and ethyl acetate to the residue, stir the mixture for 40 minutes, and separate the organic phase. The aqueous phase was extracted twice with 300 mL of ethyl acetate. After combining the organic phases, the organic phase was washed with water (300 mL) twice and dried overnight with sodium sulfate. The obtained crude product (310 g) was directly used in the next reaction.

[0024] Add chlorobenzene (1000 mL) to a 5000 mL three-necked round-bottomed flask, then add the above crude product 1-bromo-4'-(2,2-dimethoxyethyl)benzene (310 g), phosphoric a...

Embodiment 3

[0026] Add N,N-dimethylformamide (800 mL) into a 2000 mL three-necked round bottom flask, then add p-o-bromophenol (210 g, 1.213 mol), potassium carbonate (750 g, 5.426 mol) and 2-Chloroacetaldehyde dimethyl acetal (222 g, 1.78 mol). Stirring was started and heated to reflux for 30 hours. TLC and GC followed the reaction. After the reaction was completed, most of the N,N-dimethylformamide was distilled off. Add 800 mL each of water and ethyl acetate to the residue, stir the mixture for 55 minutes, and separate the organic phase. The aqueous phase was extracted twice with 300 mL of ethyl acetate. After combining the organic phases, the organic phase was washed with water (300 mL) twice and dried overnight with sodium sulfate. The resulting crude product (282 g) was directly used in the next reaction.

[0027] Add chlorobenzene (1000 mL) to a 5000 mL three-necked round-bottomed flask, then add the above crude product 1-chloro-4'-(2,2-dimethoxyethyl)benzene (282 g), phosphori...

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Abstract

The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of 7-bromobenzofuran. The preparation method comprises the following steps: reacting ortho-bromophenol and 2-bromo-1,1-dimethoxyethane or 2-chloro-1,1-dimethoxyethane in a proper solvent under the action of alkali at proper temperature for several hours to generate 1-bromo-2'-(2,2-dimethoxyethyl)benzene; and under the action of acid, carrying out cyclization reaction on the 1-bromo-2'-(2,2-dimethoxyethyl)benzene in a corresponding solvent by heating, and purifying to obtain the 7-bromobenzofuran.By adopting the two-step process to prepare the 7-bromobenzofuran, the method is simple to operate, lowers the production cost, is easy for industrialized amplification, and prevents the heavy metal catalyst from polluting the environment.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of 7-bromobenzofuran. Background technique [0002] Benzofuran and its derivatives are very important organic compounds, which have high biological activity and widely exist in the framework of many natural products. Therefore, the synthesis of benzofuran and its derivatives has received extensive attention. There are a lot of literatures reporting the synthesis of benzofuran ring. The classic synthesis of benzofuran is obtained by O-alkylation of salicylaldehyde with chloroacetic acid followed by dehydration. In recent years, it is also obtained by O-alkylation of phenol and its derivatives with chloroacetaldehyde or bromoacetaldehyde, and then dehydration under the action of acid. [0003] Benzofuran compounds have various biological activities such as antihistamine, antitumor and antiarrhythmia, and many of these active compounds are expected to become dr...

Claims

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Application Information

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IPC IPC(8): C07D307/79
CPCC07D307/79
Inventor 曹惊涛韩猛来新胜
Owner SHANDONG YOUBANG BIOCHEM TECH
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