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Preparation method of 4-(imidazole-1-yl) phenol

A technology of phenol and imidazole, applied in the field of preparation of 4-phenol, can solve the problems of difficult extraction, high difficulty, poor product color and the like, and achieves the effects of low price, low cost and satisfying market demand

Active Publication Date: 2021-10-19
上海瀚诺威生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Existing synthesis of 4-(imidazol-1-yl)phenol is difficult in post-treatment, the product forms hydrogen bonds with water, which makes it difficult to extract in the water phase, and the color of the product caused by copper ion residues is not good (partial green-gray or brown-gray) problem

Method used

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  • Preparation method of 4-(imidazole-1-yl) phenol
  • Preparation method of 4-(imidazole-1-yl) phenol
  • Preparation method of 4-(imidazole-1-yl) phenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Step (1): In the reactor, add 1kg p-bromoanisole, 0.5kg imidazole, 70g cuprous oxide, 1kg potassium carbonate and 2LNMP, and stir. The reaction temperature was raised to 120°C and reacted for 12 hours. After the reaction is completed, filter and rinse with 500 mL of ethyl acetate to remove solids; add 2 L of 8% NaOH aqueous solution and stir, and solids are generated, and then filter to remove solids. To the liquid, ethyl acetate (3x1 L) was added for extraction, and the organic phases were combined. Add saturated brine to the organic phase, stir, separate, dry, spin off the solvent, and recrystallize using methyl tert-butyl ether to obtain 500 g of 1-(4-methoxyphenyl)-1H-imidazole; rate 53%;

[0037] Step (2): In the reactor, add 0.5kg 1-(4-methoxyphenyl)-1H-imidazole, dissolve in dichloromethane, stir, cool the system to 0°C in an ice-salt bath, and under nitrogen protection, Add 4.3L of 1.0M BBr dropwise 3 dichloromethane solution. After dropping, the temperatur...

Embodiment 2

[0041] Step (1): In the reactor, add 1kg p-bromoanisole, 0.5kg imidazole, 70g cuprous oxide, 1kg cesium carbonate and 2LNMP, and stir. The reaction temperature was raised to 120°C and reacted for 12 hours. After the reaction is completed, filter, add NaOH aqueous solution, stir, and filter. Extract with ethyl acetate, and combine the organic phases. Add saturated brine to the organic phase, stir, separate liquids, dry, spin off the solvent, and crystallize methyl tert-butyl ether to obtain 700 g of 1-(4-methoxyphenyl)-1H-imidazole; yield 74 %.

[0042] Step (2) is the same as in Example 1.

Embodiment 3

[0044] Step (1): In the reactor, add 1kg p-bromoanisole, 0.5kg imidazole, 70g cuprous iodide, 1kg cesium carbonate and 2LDMF, and stir. The reaction temperature was raised to 120°C and reacted for 12 hours. After the reaction is completed, filter, add NaOH aqueous solution, stir, and filter. Extract with ethyl acetate, and combine the organic phases. Add saturated brine to the organic phase, stir, separate liquids, dry, spin off the solvent, crystallize methyl tert-butyl ether to obtain 450 g of 1-(4-methoxyphenyl)-1H-imidazole; yield 48 %.

[0045] Step (2) is the same as in Example 1.

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Abstract

The invention discloses a preparation method of 4-(imidazole-1-yl) phenol, and belongs to the field of in vitro diagnosis. The method comprises the following steps: by taking p-bromoanisole and imidazole as raw materials, carrying out Ullmann reaction in the presence of a catalyst, an alkali and a reaction solvent, extracting to obtain an organic phase after the reaction is finished, adding a saturated saline solution into the organic phase, stirring, separating liquid, drying, and crystallizing by using methyl tert-butyl ether to obtain 1-(4-methoxyphenyl)-1H-imidazole; and carrying out demethylation on the 1-(4-methoxyphenyl)-1H-imidazole by using boron tribromide, and recrystallizing to obtain the 4-(imidazole-1-yl) phenol. According to the method, the post-treatment process is simple, a large amount of solvent extraction and column chromatography purification are not needed, the product can be obtained only through recrystallization, and the prepared product is free of copper ion residues, white in appearance and capable of better meeting the market requirement.

Description

technical field [0001] The invention belongs to the field of in vitro diagnosis, in particular to a preparation method of 4-(imidazol-1-yl)phenol. Background technique [0002] The luminol system can be oxidized by some oxidants under alkaline conditions, and a chemiluminescent reaction occurs, radiating chemiluminescence with a maximum emission wavelength of 425nm. The luminol system can be widely used in criminal investigation, bioengineering, chemical tracing and other fields . Among them, 4-(imidazol-1-yl)phenol is a luminol system enhancer, which is very important for in vitro diagnosis. [0003] At present, the synthetic methods of 4-(imidazol-1-yl) phenol include: 1) Wen Chen et al. (Journal of the American Chemical Society, 2007,129,13879-13886) reported that taking p-bromophenol and imidazole as raw materials, through One-step synthesis of 4-(imidazol-1-yl)phenol by Kalman reaction. 2) Pratt, Derek A. et al. (Organic Letters, 2005, 7, 2735-2738) reported the synt...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/60
CPCC07D233/60
Inventor 潘得成钟佩岑马迪祝长斌
Owner 上海瀚诺威生物科技有限公司
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