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Synthesis method of 3-bromomethyl-4-bromoacetophenone

A technology of bromoacetophenone and synthesis method, which is applied in the preparation of carbonyl compounds, chemical instruments and methods, and preparation of carbonyl compounds by condensation, etc., can solve the problems of high price, high total cost, low yield and the like

Pending Publication Date: 2021-01-22
武汉利昌医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] This route uses Weber amine and condensation reagents, which are more expensive, and the last step of the carbonyl α-position and the methyl group can be brominated, and it is easy to replace more, the selectivity is not good, the yield is low, and the total cost is high.

Method used

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  • Synthesis method of 3-bromomethyl-4-bromoacetophenone
  • Synthesis method of 3-bromomethyl-4-bromoacetophenone
  • Synthesis method of 3-bromomethyl-4-bromoacetophenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Synthesis of compound Ⅱ

[0048]At room temperature (20-25°C), dissolve 185.02g of o-bromobenzaldehyde in 185ml of acetamide, and add catalyst 154.66g of thionyl chloride dropwise at a temperature of 15-25°C. After dropping, keep warm at 20-25°C for reaction , monitor the reaction in the liquid phase, and the reaction is complete in about 10-13 hours. After the reaction is completed, add 300 g of ice water dropwise at a temperature of 0-30 ° C to destroy, add 600 ml of dichloroethane for extraction, and after liquid separation, wash the organic phase with 200 ml of water once. Liquid separation, dichloromethane was distilled off the organic phase under reduced pressure, ethyl acetate:petroleum ether=1:5 was added for recrystallization, and 190.5 g of the product was obtained as a light yellow solid with a content of 99.62% and a yield of 83.58%.

Embodiment 2

[0050] Synthesis of compound Ⅱ

[0051] At room temperature (20-25°C), dissolve 185.02g of o-bromobenzaldehyde and 70.89g of acetamide in 555ml of dichloromethane, and add catalyst 154.66g of thionyl chloride dropwise at a temperature of 15-25°C. , keep warm at 20-25°C, monitor the reaction in the liquid phase, and the reaction is complete in about 10-13 hours. After the reaction, control the temperature at 0-30°C and add 300g of ice water dropwise to destroy it. Liquid, dichloromethane was distilled off the organic phase under reduced pressure, ethyl acetate:petroleum ether=1:5 solvent was added for recrystallization, and 178.87g of the product was obtained as a light yellow solid with a content of 99.47% and a yield of 78.36%.

Embodiment 3

[0053] Synthesis of Compound Ⅲ-a

[0054] At room temperature (20-25°C), add 113.53g of compound II to 568ml of dichloromethane to dissolve, then add 65.18g of trimethylchlorosilane, 67.16g of 1,1,3,3 -Tetramethyldisiloxane, react at 30-40°C after addition, monitor the reaction in liquid phase, stop the reaction until the compound II is 0-3%, lower the temperature, add 300ml water at 0-20°C and stir for 30 minutes, separate the liquid, The organic phase was washed twice with water, 150ml each time, the solvent was recovered under reduced pressure, and the concentrated dry matter was recrystallized by adding ethyl acetate:petroleum ether=1:2.5 solvent, filtered by suction, and dried to obtain 100.68g of white crystal compound III-a, the content of 99.30%, yield 80.78%, compound Ⅲ-a, 1HNMR (400MHz, CDCl3) δ8.05 (s, 1H), 7.75 (d, J=8.4Hz, 1H), 4.73 (s, 2H), 2.60 (s , 3H).

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Abstract

The invention discloses a synthesis method of 3-bromomethyl-4-bromoacetophenone, and belongs to the technical field of organic synthesis. An acylation reaction is carried out on o-bromobenzaldehyde and acetamide under the action of a catalyst C1 to obtain a compound II; wherein the reaction temperature is 0-80 DEG C, the molar ratio of the o-bromobenzaldehyde to the catalyst C1 is 1: 1.0-2.0, theweight-volume ratio of the o-bromobenzaldehyde to the acetamide is 1: 0.28-5.0 g / mL, and the catalyst C1 is selected from phosphorus oxybromide, phosphorus oxychloride, dibromo sulfoxide, thionyl chloride or disulfuryl chloride; the compound II is reacted with an alkyl halogen silane reagent in a solvent S2 under the action of a catalyst C2 to obtain a compound III; wherein the reaction temperature is 0-110 DEG C, the molar ratio of the compound II to the catalyst C2 to the alkyl halide silane is 1: 0.5-2.0: 1.0-5.0, and the catalyst C2 is polymethylhydrosiloxane or 1, 1, 3, 3-tetramethyldisiloxane.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a synthesis method of 3-bromomethyl-4-bromoacetophenone. Background technique [0002] 3-Bromomethyl-4-bromoacetophenone, molecular formula C 9 h 8 Br 2 O, relative molecular weight 291.97, appearance is white crystal, its structural formula is as follows: [0003] [0004] Hepatitis C virus (HCV) has the characteristics of strong infectivity, complex transmission route, wide prevalence and high incidence rate. HCV infection is a serious threat to human health. At present, there are about 185 million people infected in the world, and the infection rate is about 3%. In addition, there are about 3-4 million new cases of HCV infection every year. HCV is a positive-strand RNA virus belonging to the family Flaviviridae. Therefore, the research on NS5A as the target has become a research hotspot at present. Velpatasvir (Velpatasvir, CAS: 1377049-84-7) is a pan-genotyp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/63C07C49/80C07C45/45C07C49/86
CPCC07C45/63C07C45/455C07C49/86C07C49/80
Inventor 丁四海林晓辉
Owner 武汉利昌医药科技有限公司
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