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Novel method for synthesizing 3, 5-dinitrobenzyl chloride

A technology of dinitrobenzyl chloride and a new method, which is applied in the field of synthesizing 3,5-dinitrobenzyl chloride, can solve the problems of expensive reducing reagents, complicated recycling, environmental threats, etc., and achieve good product yields, The effect of easy purification and simplified post-processing

Inactive Publication Date: 2020-07-10
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reducing reagents used in these two methods are expensive, and there is a large amount of use, and recycling requires complicated treatment, which poses a threat to the environment

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment 1: the preparation of 3,5-dinitrobenzyl alcohol

[0021] Add 200 mL of tetrahydrofuran to a four-neck flask, add 52.0 g of 3,5-dinitrobenzoyl chloride and 10.0 g of anhydrous zinc chloride and stir, and cool the water bath to 10°C. 15 g of triethylamine was slowly added dropwise thereto, and then 12 g of sodium borohydride was added in batches, stirred at room temperature for 1 h, then heated up, and refluxed for 5 h. After cooling to room temperature, 50 mL of methanol was added to precipitate a solid. Filter, wash the filter cake with methanol, combine the filtrates, remove the solvent, disperse the residue with 50mL ethyl acetate and 30mL water, add 20% sulfuric acid solution to neutralize to pH=3~4, separate the oil layer, and use 25mL water layer Ethyl acetate × 2 extraction. The oil layers were combined, and the solvent was removed by rotary evaporation to obtain a viscous black liquid, which was recrystallized from petroleum ether-ethyl acetate mixtu...

Embodiment 2

[0022] Embodiment 2: the preparation of 3,5-dinitrobenzyl alcohol

[0023] Add 160 mL of tetrahydrofuran to a four-necked flask, add 52.0 g of 3,5-dinitroacyl chloride and 12 g of zinc sulfate, stir, and cool down to 10°C in a cold water bath. 20 g of triethylamine was slowly added dropwise thereto, and then 8.5 g of sodium borohydride was added in batches, stirred at room temperature for 1 h, then heated up, and refluxed for 5 h. Cool to room temperature, add 50 mL of methanol, precipitate solid, filter, wash the filter cake with methanol, combine the filtrates, remove the solvent, disperse the residue with 50 mL of ethyl acetate and 30 mL of water, add 20% sulfuric acid solution to neutralize to pH=3 ~4, the oil layer was separated, and the water layer was extracted with 25 mL of ethyl acetate x 2. The oil layers were combined, and the solvent was removed by rotary evaporation to obtain a viscous black liquid, which was recrystallized from petroleum ether-ethyl acetate and ...

Embodiment 3

[0024] Embodiment 3: the preparation of 3,5-dinitrobenzyl alcohol

[0025] Add 60mL of tetrahydrofuran and 100mL of toluene to the mixture of 60mL of tetrahydrofuran and 100mL of toluene, add 52.0g of 3,5-dinitroacyl chloride and 16g of zinc sulfate into the four-neck flask, stir, and cool the water bath to 10°C. Slowly add 25 g of triethylamine dropwise thereto, and then add 10 g of sodium borohydride in batches, stir at room temperature for 1 h, then raise the temperature, and reflux for 5 h. Cool to room temperature, add 50mL of methanol, precipitate solid, filter, wash the filter cake with methanol, combine the filtrate, remove low boiler methanol, tetrahydrofuran, etc., neutralize the residue with 20% sulfuric acid solution to pH=3~4, separate The oily layer was extracted, and the aqueous layer was extracted with 25 mL of ethyl acetate × 2. The oil layers were combined, and the solvent was removed by rotary evaporation, and the residue was recrystallized from petroleum e...

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Abstract

The invention provides a novel method for synthesizing 3, 5-dinitrobenzyl chloride. The novel method comprises the following steps: a, carrying out reduction reaction on 3, 5-dinitrobenzoyl chloride and a reducing agent in a first solvent to obtain 3, 5-dinitrobenzene methanol; and b, carrying out chlorination reaction on the 3, 5-dinitrobenzene methanol, a chlorination reagent and a catalyst in asecond solvent to obtain the 3, 5-dinitrobenzyl chloride. According to the method, the reduction process of the 3, 5-dinitrobenzoyl chloride is remarkably improved, a simple reducing agent is used, nitro reduction is avoided under the assistance of Lewis acid and Lewis alkali, and the reaction selectivity and the product yield are improved.

Description

technical field [0001] The invention belongs to the field of preparation of a class of pesticides and pharmaceutical intermediates, in particular to a new method for synthesizing 3,5-dinitrobenzyl chloride. Background technique [0002] 3,5-Dinitrobenzyl chloride is an intermediate that can be used in the manufacture of medicine and functional materials. For example, tetrazole, oxadiazole, and thiadiazole drugs used for anti-tuberculosis; anti-mycobacterial and anti-protozoal active substances, drugs for the treatment of arteriosclerosis, anti-nitric oxide synthase inhibitors; cyclic peptides similar Light-actuated molecular brakes based on polarizable amine linear optical liquid crystal materials. [0003] Benzyl chloride is generally synthesized with toluene as a raw material through rectification after chlorination, and 3,5-dinitrobenzyl chloride cannot be obtained by this method, because the required raw material 3,5-dinitrotoluene is not easy to prepare . It is repor...

Claims

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Application Information

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IPC IPC(8): C07C201/12C07C205/19C07C205/11
CPCC07C201/12C07C205/19C07C205/11
Inventor 卜洪忠左杭冬马鸿飞李玉峰
Owner NANJING UNIV OF TECH
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