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Preparation method of 5-bromobenzofuranone

A technology of furanone and bromoacetophenone, which is applied in the field of preparation of 5-bromobenzofuranone, can solve the problems of low yield, low yield, low yield, etc.

Pending Publication Date: 2022-06-03
八叶草健康产业研究院厦门有限公司 +1
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Problems solved by technology

In 2001, Safdar Hayat et al reported the conversion of 4-bromo-2-methylbenzoic acid in NaBrO 3 -NaHSO 3 A method for generating 5-bromobenzofuranone by oxidation under certain conditions, the yield of this method is not high, being 42% (Safdar, H.; Rahman, M.lqbalC.Ernst, B.; An improved method for the synthesis ofY- lactones using Sodium Bormate and Sodium Hydrogen Sulfite[J]; Tetra.Lett.2001,42:1647-1649); in 2002, Jiang Fangfang and others reported that o-xylene was used as raw material through bromination reaction and catalytic oxidation reaction to prepare 5-Bromobenzofuranone, but the yield of 5-bromobenzofuranone is 69.1%, which is also not high (Jiang Fangfang, Wei Guobing. Research on the synthesis method of 5-bromobenzofuranone[J].Journal of Hunan University ,2002,29(3):12-15)
[0005] In summary, the existing method for preparing 5-bromobenzofuranone has the problem that the yield is not high

Method used

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  • Preparation method of 5-bromobenzofuranone
  • Preparation method of 5-bromobenzofuranone

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preparation example Construction

[0024] The invention provides a preparation method of 5-bromobenzofuranone, comprising the following steps:

[0025] Mix 2-hydroxy-5-bromoacetophenone, bromination reagent, catalyst and first organic solvent, and carry out bromination reaction to obtain 2-bromo-1-(5-bromo-2-hydroxyphenyl)-ethanone ;

[0026] The 2-bromo-1-(5-bromo-2-hydroxyphenyl)-ethanone, the organic base and the second organic solvent are mixed to carry out a cyclization reaction to obtain 5-bromobenzofuranone.

[0027] Unless otherwise specified, the preparation raw materials used in the present invention are all commercially available.

[0028] In the present invention, the synthetic route of described 5-bromobenzofuranone is shown in formula 1:

[0029]

[0030] In the present invention, 2-hydroxy-5-bromoacetophenone, a bromination reagent, a catalyst and a first organic solvent are mixed, and a bromination reaction is carried out to obtain 2-bromo-1-(5-bromo-2-hydroxyphenyl)- ethyl ketone. In the...

Embodiment 1

[0038] Add 10g 2-hydroxy-5-bromoacetophenone in the reactor, dissolve it in the solvent that 50mL ethyl acetate and 50mL 1,2-dichloroethane form, then add 7.43g liquid bromine, 0.8g successively copper bromide, the temperature of the reaction kettle was heated to 100 ° C and stirred for 12 h, and the reaction progress was monitored in the gas phase. After the reaction, the reaction kettle was lowered to room temperature, and the solid impurities in the reaction system were removed by filtration to obtain a filtrate, and the filtrate was rotary-evaporated at 40 ° C until the solvent was evaporated to dryness to obtain 2-bromo-1-(5-bromo-2- Hydroxyphenyl)-ethanone crude product. Then, 20 mL of water was added to the crude product of 2-bromo-1-(5-bromo-2-hydroxyphenyl)-ethanone to redissolve it, 60 mL of dichloromethane was added for extraction, and the layers were separated to obtain a dichloromethane phase. The chloromethane phase was washed with 60 mL of brine, then the dichl...

Embodiment 2

[0041] Add 20g of 2-hydroxy-5-bromoacetophenone to the reactor, dissolve it in the solvent composed of 100mL of ethyl acetate and 100mL of chloroform, then add 14.86g of hydrobromic acid and 1.5g of iron powder successively, The temperature of the reaction kettle was heated to 80°C and the reaction was stirred for 15h, and the reaction progress was monitored in the gas phase. After the reaction, the reaction kettle was lowered to room temperature, and the solid impurities in the reaction system were removed by filtration to obtain a filtrate. The filtrate was rotary-evaporated at 35°C until the solvent was evaporated to dryness to obtain 2-bromo-1-(5-bromo-2- Hydroxyphenyl)-ethanone crude product. Then, 40 mL of water was added to the crude product of 2-bromo-1-(5-bromo-2-hydroxyphenyl)-ethanone to redissolve it, and 120 mL of chloroform was added for extraction, and the layers were separated to obtain a chloroform phase. The chloromethane phase was washed with 120 mL of brin...

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Abstract

The invention relates to the technical field of synthesis of medical intermediates, and provides a preparation method of 5-bromobenzofuranone. The preparation method provided by the invention comprises the following steps: mixing 2-hydroxy-5-bromoacetophenone, a bromination reagent, a catalyst and a first organic solvent, and carrying out bromination reaction to obtain 2-bromo-1-(5-bromo-2-hydroxyphenyl)-ethanone; and mixing the 2-bromine-1-(5-bromine-2-hydroxyphenyl)-ethanone, organic alkali and a second organic solvent, and carrying out cyclization reaction to obtain the 5-bromobenzofuranone. According to the method, the 2-hydroxy-5-bromoacetophenone is used as a raw material, the bromination reaction and the cyclization reaction are sequentially performed to prepare the 5-bromobenzofuran, the operation is simple, and the yield and the purity are relatively high. Furthermore, the raw materials required by the method are easier to obtain, the reaction time is short, and the complexity of the preparation method is more favorably reduced.

Description

technical field [0001] The invention relates to the technical field of synthesis of pharmaceutical intermediates, in particular to a preparation method of 5-bromobenzofuranone. Background technique [0002] Depressive disorder refers to a type of mood disorder caused by various reasons with significant and persistent depression as the main clinical feature. It is a chronic mental disease with high incidence, high recurrence rate and high disability rate. cognitive and behavioral changes, and some patients have self-injury and suicidal behaviors. Most of the disease has acute or subacute onset, and the average age of onset is 20 to 30 years old. Almost every age group has the possibility of suffering from depressive disorder, and there are more women than men. The average duration of a single depressive episode is about 16 weeks, and recovery from the episode takes an average of about 20 weeks. Without treatment, the course of the disease typically lasts 6 months or more. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/83C07C45/63C07C49/825
CPCC07D307/83C07C45/63C07C49/825
Inventor 汤须崇赵应伟林青杨婷
Owner 八叶草健康产业研究院厦门有限公司
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