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Process for preparing 2-chloro-5-nitro phenyl -4'-methoxy benzophenone

A technology of methoxybenzophenone and nitrophenyl, which is applied in the field of preparation of 2-chloro-5-nitrophenyl-4'-methoxybenzophenone, can solve complicated operations and difficult product separation , low yield and other problems, to achieve the effect of high content, good product purity and improved yield

Inactive Publication Date: 2008-05-07
SINOPHARM CHEM REAGENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of this invention is to provide the preparation method of mono and 2-chloro-5-nitrophenyl-4'-methoxybenzophenone, to overcome the complex operation in the prior art, product separation difficulty, the shortcoming of low yield

Method used

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  • Process for preparing 2-chloro-5-nitro phenyl -4'-methoxy benzophenone
  • Process for preparing 2-chloro-5-nitro phenyl -4'-methoxy benzophenone

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Add 500ml of dichloromethane to a 1000ml four-necked flask equipped with a stirrer and a thermometer, and add 87.4g (0.3969mol) of 2-chloro-5-nitrobenzoyl chloride 72.0g (0.6658mol) of anisole under stirring, and the reaction solution Cool to -8°C ~ -12°C, add 72.0g (0.5560mol) of anhydrous aluminum trichloride, maintain the temperature, react for 8 hours; drop 240ml of 10% hydrochloric acid in 2 hours, let stand overnight; separate the water phase , dichloromethane solvent was distilled off, ethyl acetate / ethanol (V:V=1:1) mixed solvent 350ml was added to the residue, heated to reflux for 2 hours, cooled, white crystals were precipitated, filtered and dried to obtain the target product 2 -Chloro-5-nitrophenyl-4'-methoxybenzophenone 68.5g, yield 59.1%, analysis result: purity ≥ 98.2% (HPLC), melting point 111.1 ° C ~ 112.7 ° C (literature value: 111 ~ 113 ℃), NMR identification structure:

[0023] 1 H NMR ([D 6 ]DMSO 400MHz)

[0024] δ: 3.87 (s, 3H) δ: 6.90 (d, 2H) ...

Embodiment 2

[0027] In a 1000ml four-necked flask equipped with a stirrer and a thermometer, add 500ml of methylene chloride, add 87.4g (0.3969mol) of 2-chloro-5-nitrobenzoyl chloride, 80.0g (0.7398mol) of anisole under stirring, Cool the reaction solution, add 75.0g (0.5792mol) of anhydrous aluminum trichloride at -10°C to -15°C, and maintain the temperature for 15 hours; add 220ml of 10% hydrochloric acid dropwise within 2 hours, and let it stand overnight; phase, evaporate the dichloromethane solvent, add 500ml ethyl acetate / ethanol (V:V=1:1) mixed solvent to the residue, heat and reflux for 2 hours, cool, and precipitate white crystals, filter, and dry to obtain 2- Chloro-5-nitrophenyl-4'-methoxybenzophenone 71.1g, yield 61.4%, analysis result: purity ≥ 98.5% (HPLC), melting point 111.3°C-112.7°C.

Embodiment 3

[0029] Add 55 l of methylene chloride in a 100 l reactor equipped with a stirrer and a thermometer, add 8.74kg (39.68mol) of 2-chloro-5-nitrobenzoyl chloride, 7.5kg (69.35mol) of anisole under stirring , the reaction solution was cooled, and 7.2kg (55.60mol) of anhydrous aluminum trichloride was added at -8°C to -12°C, and the temperature was maintained for 10 hours; 24 liters of 10% hydrochloric acid was added dropwise within 2 hours, and allowed to stand overnight; Remove the water phase, evaporate the dichloromethane solvent, add 40 l of ethyl acetate / ethanol (V:V=1:1) to the residue, heat to reflux for 2 hours, cool, and precipitate white crystals, filter, and dry 7.01 kg of 2-chloro-5-nitrophenyl-4'-methoxybenzophenone was obtained with a yield of 60.5%. Analysis results: purity ≥ 98.5% (HPLC), melting point 111.2°C-112.7°C.

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Abstract

The present invention discloses one kind of 2-chloro-5-nitrobenzyl-4'-methoxy benzophenone. The present invention obtains the target product by using 2-chloro-5-nitro benzoyl as main material and anhydrous aluminum trichloride as catalyst, and through the Friedel-Crafts acylation reaction with methyl phenoxide in alkyl halide as reaction solvent, hydrochloric acid hydration and re-crystallization. The said preparation process can obtain 2-chloro-5-nitrobenzyl-4'-methoxy benzophenone product in purity over 98 %, yield over 58 % and melting point of 111-113 deg.c. The present invention has simple operation, easy product separation and high yield, and is suitable for industrial production.

Description

technical field [0001] The present invention relates to a kind of preparation method of 2-chloro-5-nitrophenyl-4'-methoxybenzophenone. Background technique [0002] 2-Chloro-5-nitrophenyl-4'-methoxybenzophenone is an important intermediate in organic synthesis, especially as a pharmaceutical intermediate in the preparation of liver mitochondrial enzyme inhibitors and antipyretics. wide application prospects. Its structural formula is as follows: [0003] [0004] In the prior art, WO 03-0228042 discloses a reaction of 2-chloro-5-nitrobenzoic acid as a raw material with phosphorus pentachloride to obtain 2-chloro-5-nitrobenzoyl chloride. In the presence of aluminum chloride, the Friedel-Crafts acylation reaction with anisole was carried out, and the reaction product was recrystallized to obtain 2-chloro-5-nitrophenyl-4'-methoxybenzophenone with a yield of 41%. . In the preparation method of this patent, the catalyst is added in batches, the reaction process is cumberso...

Claims

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Application Information

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IPC IPC(8): C07C205/45C07C201/12
Inventor 施沁清詹家荣施险峰蒋旭亮
Owner SINOPHARM CHEM REAGENT
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