Chemical synthesis method of 3-bromo-2-nitrobenzaldehyde

A technology for the chemical synthesis of nitrobenzaldehyde, which is applied in chemical instruments and methods, organic chemistry, and the preparation of organic compounds. It can solve problems such as low yield and difficult separation, and achieve high yield, low price, and high-efficiency synthesis. Effect

Active Publication Date: 2014-06-25
唐山金硕化工有限公司
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  • Abstract
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Problems solved by technology

[0006] The purpose of the present invention is to provide a new high-efficiency chemical synthesis route in order to overcome the defects of low yield and difficult separation in the existing oxidation synthesis method

Method used

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  • Chemical synthesis method of 3-bromo-2-nitrobenzaldehyde
  • Chemical synthesis method of 3-bromo-2-nitrobenzaldehyde
  • Chemical synthesis method of 3-bromo-2-nitrobenzaldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Synthesis of 2-(3-bromo-2-nitrobenzaldehyde)-dimethyl malonate:

[0026] Add 150mL of N,N-dimethylformamide into the three-necked flask, add 30.0g of 1,3-dibromo-2-nitrobenzene and 28.0g of dimethyl malonate to dissolve, and add 15.0g of sodium carbonate. The temperature of the system was raised to 60°C, and the reaction was detected by thin-layer chromatography to the end. Add 1L of water, extract with ethyl acetate (100mL×3), combine the organic phases, wash with water, wash with saturated brine, dry over anhydrous sodium sulfate, and concentrate to obtain 2-(3-bromo-2-nitrobenzaldehyde)-malonic acid Dimethyl ester 37.1g (96.5%).

[0027] Synthesis of 2-(3-bromo-2-nitrobenzaldehyde)-acetic acid:

[0028] Add 250 mL of acetone to the three-neck flask, add 36.0 g of dimethyl 2-(3-bromo-2-nitrobenzaldehyde)-malonate to dissolve, and add 25 mL of 8M hydrochloric acid. Heated to reflux and reacted, and the reaction was detected by thin layer chromatography until the end...

Embodiment 2

[0036] Synthesis of 2-(3-bromo-2-nitrobenzaldehyde)-dimethyl malonate:

[0037] Add 150 mL of dimethyl sulfoxide to the three-neck flask, add 30.0 g of 1,3-dibromo-2-nitrobenzene and 28.0 g of dimethyl malonate to dissolve, and add 15.0 g of sodium carbonate. The temperature of the system was raised to 50°C, and the reaction was detected by thin-layer chromatography to the end. Add 1L of water, extract with ethyl acetate (100mL×3), combine the organic phases, wash with water, wash with saturated brine, dry over anhydrous sodium sulfate, and concentrate to obtain 2-(3-bromo-2-nitrobenzaldehyde)-malonic acid Dimethyl ester 37.8g (98.3%).

[0038] Synthesis of 2-(3-bromo-2-nitrobenzaldehyde)-acetic acid:

[0039] Add 250 mL of tetrahydrofuran into the three-necked flask, add 36.0 g of 2-(3-bromo-2-nitrobenzaldehyde)-malonate dimethyl ester to dissolve, and add 25 mL of 6M hydrochloric acid. Heated to reflux and reacted, and the reaction was detected by thin layer chromatograph...

Embodiment 3

[0047] Synthesis of 2-(3-bromo-2-nitrobenzaldehyde)-dimethyl malonate:

[0048] Add 150mL of N,N-dimethylformamide into the three-necked flask, add 30.0g of 1,3-dibromo-2-nitrobenzene and 28.0g of dimethyl malonate to dissolve, and add 18.0g of potassium carbonate. The temperature of the system was raised to 60°C, and the reaction was detected by thin-layer chromatography to the end. Add 1L of water, extract with ethyl acetate (100mL×3), combine the organic phases, wash with water, wash with saturated brine, dry over anhydrous sodium sulfate, and concentrate to obtain 2-(3-bromo-2-nitrobenzaldehyde)-malonic acid Dimethyl ester 37.4g (97.3%).

[0049] Synthesis of 2-(3-bromo-2-nitrobenzaldehyde)-acetic acid:

[0050]Add 250 mL of acetone to the three-neck flask, add 36.0 g of dimethyl 2-(3-bromo-2-nitrobenzaldehyde)-malonate to dissolve, and add 25 mL of 10M hydrochloric acid. Heated to reflux and reacted, and the reaction was detected by thin layer chromatography until the ...

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Abstract

The invention relates to a chemical synthesis method of 3-bromo-2-nitrobenzaldehyde. The chemical synthesis method is characterized by using 1,3-dibromo-2-nitrobenzene as a raw material and carrying out five-step reactions including substitution, decarboxylation, oxidation, reduction and hydroformylation, and comprises the following steps of adding 1,3-dibromo-2-nitrobenzene, dimethyl malonate and alkali to an organic solvent to react to prepare 2-(3-bromo-2-nitrobenzaldehyde)-dimethyl malonate; dissolving 2-(3-bromo-2-nitrobenzaldehyde)-dimethyl malonate obtained in the former step in a tetrahydrofuran or acetone solvent, and adding a hydrochloric acid solution to react to prepare 2-(3-bromo-2-nitrobenzaldehyde)-acetic acid; adding a sodium hydroxide water solution and potassium permanganate to react to obtain 3-bromo-2-nitrobenzoic acid; dissolving 3-bromo-2-nitrobenzoic acid in the tetrahydrofuran solvent, and adding borane tetrahydrofuran to react to obtain 3-bromo-2-nitrobenzyl alcohol; adding 3-bromo-2-nitrobenzyl alcohol to a dichloromethane or 1,2-dichloroethane solvent and adding manganese dioxide to react to prepare 3-bromo-2-nitrobenzaldehyde. The synthetic route has the advantages of low cost and high yield.

Description

technical field [0001] The invention relates to a chemical synthesis method of 3-bromo-2-nitrobenzaldehyde. Background technique [0002] 3-Bromo-2-nitrobenzaldehyde is an important pharmaceutical intermediate, especially in cardiovascular and anticancer drugs, so the research on the synthesis of this compound has important practical significance. [0003] At present, its synthesis is mainly prepared by oxidation of 3-bromo-2-nitrotoluene, and the reaction formula is as follows: [0004] [0005] The oxidant in this step uses sodium periodate, which is expensive, and it is difficult to control the oxidation of the methyl group to stay in the aldehyde group. The yield of the reaction is only 35%, which makes the separation difficult. Contents of the invention [0006] The purpose of the present invention is to provide a new high-efficiency chemical synthesis route in order to overcome the defect of low yield and difficult separation in the existing oxidation synthesis m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C205/44C07C201/12
Inventor 朱金丽汤艳峰王淼孙同明丁津津田亮朱亮亮洪传霞
Owner 唐山金硕化工有限公司
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