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Bromo-2, 4'-dihydroxy diphenyl ether compound and its synthesizing method

A technology of dihydroxydiphenyl ether and synthesis method, which is applied in ether preparation, organic chemistry, drug combination, etc., and can solve problems such as complex extraction process, limited sources, and difficulties

Inactive Publication Date: 2006-05-24
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Triclosan itself is safe and non-toxic to the human body, but at present the production of triclosan in the world is widely using 2,4-dichlorophenol and 2,5 dichloronitrobenzene as raw materials, after condensation, reduction, diazotization, The process of hydrolysis and separation, etc., in this process makes the product very easy to carry highly toxic impurities, polychlorinated dibenzofuran compounds 2, dioxin-like compounds 3
[0017] In 2001, Natalia et al. also mentioned in J.Nat.Prod (2001, 64, 151) that in addition to isolating compounds 7 and 8 from Dysides marine sponges, they also isolated two dioxin-like compounds 11, 12. This also brings difficulties to the separation and purification of natural polybrominated 2,2′-dihydroxydiphenyl ethers
[0021] In summary, although the natural brominated 2,2'-dihydroxydiphenyl ether has good antibacterial activity, the isolated brominated 2,2'-dihydroxydiphenyl ether has Bromine atoms and hydroxyl groups may generate dioxin-like compounds under certain conditions; and the sources of natural polybrominated 2,2'-dihydroxydiphenyl ethers are limited, the extraction process is complicated, and the cost is relatively high, which makes the use of such antibacterial agents Broad application is limited

Method used

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  • Bromo-2, 4'-dihydroxy diphenyl ether compound and its synthesizing method
  • Bromo-2, 4'-dihydroxy diphenyl ether compound and its synthesizing method
  • Bromo-2, 4'-dihydroxy diphenyl ether compound and its synthesizing method

Examples

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Effect test

Embodiment 1

[0042] Embodiment 1: the preparation of 2,4'-dimethoxydiphenyl ether

[0043] (1) Add 0.2mol K to a three-necked flask with a magnetic stirrer, a thermometer and a reflux condenser 2 CO 3 , 0.009mol CuCl, 0.1mol pyridine, 0.22mol 2-methoxyphenol and 0.2mol 4-methoxychlorobenzene, react at 200°C for 20 hours, TLC detects the end point of the reaction, after the reaction, use ethyl acetate Extract (20mL×3 times), wash with 5% NaOH dilute solution (3 times), wash with water (3 times), dry, and evaporate the solvent to obtain a white solid crude product, which is recrystallized with petroleum ether 50mL, dried, and the product is Rate 46.0%.

[0044] (2) Add 0.2mol K to a three-necked flask with a magnetic stirrer, a thermometer and a reflux condenser 2 CO 3 , 0.009mol CuCl, 0.1mol pyridine, 0.22mol 2-methoxyphenol and 0.2mol 4-methoxychlorobenzene, reacted at 150°C for 15 hours, and detected the reaction end point by TLC. After the reaction, ethyl acetate Extract (20mL×3 tim...

Embodiment 2

[0045]Embodiment 2: Preparation of 2,4'-dihydroxydiphenyl ether

[0046] (1) Add 0.05mol 2,4'-dimethoxydiphenyl ether, 0.25mol hydrobromic acid and 3.0mol glacial acetic acid in a three-necked flask with a magnetic stirrer, a thermometer and a reflux condenser, heat to reflux, The end point of the reaction was detected by TLC. After the reaction, the glacial acetic acid was removed under reduced pressure, and the crude product was recrystallized with 60 mL of petroleum ether, and the product yield was 90.0%.

[0047] (2) Add 0.05mol 2,4'-dimethoxydiphenyl ether, 0.2mol hydrobromic acid and 3.0mol glacial acetic acid in a three-necked flask with a magnetic stirrer, a thermometer and a reflux condenser, heat to reflux, The end point of the reaction was detected by TLC. After the reaction, the glacial acetic acid was removed under reduced pressure, and the crude product was recrystallized with 60 mL of petroleum ether, and the product yield was 88.0%.

Embodiment 3

[0048] Embodiment 3: Preparation of 5-bromo-2,4'-dihydroxydiphenyl ether

[0049] (1) Add 0.004mol 2,4'-dihydroxydiphenyl ether, 0.080mol methylene chloride, 0.045mol ethyl acetate in a three-necked flask with a magnetic stirrer, a thermometer and a reflux condenser, after heating to reflux ( Reflux temperature 60 ℃), 0.004mol bromine is dissolved in the mixed solution that 0.080mol dichloromethane and 0.045mol ethyl acetate form, slowly drips in the three-necked flask, monitors the reaction progress with TLC (dichloromethane: ethyl acetate= 15:1, V:V), after the reaction was completed, cool to room temperature, and use 10mL 3% Na 2 S 2 o 3 The aqueous solution was washed three times, and then washed three times with water, the organic layer was separated, dried, and the solvent was evaporated to obtain a light yellow solid crude product, which was separated by column chromatography (dichloromethane:ethyl acetate=20:1, V:V) to obtain Target object, yield 75.0%; 1 HNMR (CDC...

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Abstract

The inventiona relates to bromo-2, 4í»-dihydroxyl diphenyl ether compound and its synthesizing method, using 2-methoxy phenol and 4-methoxy chlorobenzene as raw materials, and it is an antimicrobial obtained by three-step reaction, and has better antimicrobial activity to Escherichia coli, catarrh diplococcus, Staphylococcus aureus, Staphylococcus Albus, bacillus proteus, etc. and avoids producing highly toxic dioxin compound in the producing and using course, avoiding environmental pollution and damaging human health; and also overcomes the shortages that natural bromic2, 4í»-dihydroxyl diphenyl ether antimicrobial can form highly toxic dioxin compound in use on certain conditions, and the natural bromic2, 4í»-dihydroxyl diphenyl ether antimicrobial has limited source, complex extracting course and high cost..

Description

field of invention [0001] The invention relates to a halogenated diphenyl ether antibacterial agent compound and a synthesis method thereof. Background of the invention [0002] Halogenated hydroxydiphenyl ethers are a class of important fungicides and antibacterial agents, among which compound 1 triclosine (2,4,4'-trichloro-2'-hydroxydiphenyl ether) is a broad-spectrum antibacterial agent against Gram It has a strong inhibitory and killing effect on Gram-positive bacteria, Gram-negative bacteria, fungi and viruses, and is widely used in industries such as daily chemicals, textiles, building materials and plastics. [0003] [0004] Compound 1 [0005] Triclosan itself is safe and non-toxic to the human body, but at present the production of trichlorosin in the world widely uses 2,4-dichlorophenol and 2,5 dichloronitrobenzene as raw materials, after condensation, reduction, diazotization, The process of hydrolysis and separation, etc., in th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/295A61P31/00C07C41/01
Inventor 金洪王玉良杨志荣吴凯群陈淑华
Owner SICHUAN UNIV
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