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Preparation method of 2, 3-thiophenedicarboxaldehyde

A technology of dialdehyde-based thiophene and dimethyl thiophene, which is applied in organic chemistry and other fields, and achieves the effects of easy-to-obtain raw materials, low production costs, and mild reaction conditions

Active Publication Date: 2012-08-08
HENAN ACADEMY OF SCI CHEM RES INST CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Benzoyl peroxide catalyst added in batches

Method used

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  • Preparation method of 2, 3-thiophenedicarboxaldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] 2,3-Dimethylthiophene (11.22 g, 0.10 mol), benzoyl peroxide (0.24 g, 1.0 mmol), dissolved in 80 mL of carbon tetrachloride, vigorously stirred and heated to reflux, slowly Add a mixture of N-bromosuccinimide (35.60 g, 0.2 mol) and benzoyl peroxide (0.24 g, 1.0 mmol). After the addition is complete, continue the reaction for 3 h, cool to room temperature, and remove the formed butyl Diimide, add water to wash the filtrate, wash the organic layer with sodium bicarbonate solution, sodium chloride solution, dry with anhydrous potassium carbonate, evaporate the solvent by rotary evaporator, and purify the crude product by vacuum distillation to obtain the solid product 2, 20.3 g of 3-bis(bromomethyl)thiophene (yield 76%). Melting point: 49~50℃, 1 H NMR (solvent CDCl3), δ: 5.50 (2H, s), 5.29 (2H, s), 3.00 (1H, d, J=6.0 Hz), 2.72 (1H, d, J=6.0 Hz).

[0018] Hexamethylenetetramine (29.44 g, 0.21 mol) was dissolved in 100 mL of chloroform, and 2,3-bis(bromomethyl)thiophene (27...

Embodiment 2

[0020] 2,3-Dimethylthiophene (22.44 g, 0.20 mol), benzoyl peroxide (0.72 g, 3.0 mmol), dissolved in 160 mL of chloroform, stirred vigorously and heated to reflux, then slowly added in batches A mixture of N-bromosuccinimide (71.20 g, 0.4 mol) and benzoyl peroxide (0.72 g, 3.0 mmol), after the addition was complete, continue to react for 3 h, then cool to room temperature, and filter to remove the formed butanediol imide, adding water to wash the filtrate, the organic layer was washed with sodium bicarbonate solution and sodium chloride solution, dried with anhydrous potassium carbonate, the solvent was evaporated by a rotary evaporator, and the crude product was purified by vacuum distillation to obtain a solid product 2,3 - Bis(bromomethyl)thiophene 42.7 g (79% yield).

[0021] Hexamethylenetetramine (61.69 g, 0.44 mol) was dissolved in 200 mL of chloroform, and 2,3-bis(bromomethyl)thiophene (54 g, 0.2 mol) was slowly added dropwise under vigorous stirring. Heat spontaneousl...

Embodiment 3

[0023] 2,3-Dimethylthiophene (11.22 g, 0.10 mol), benzoyl peroxide (0.36 g, 1.5 mmol), dissolved in 80 mL of carbon tetrachloride, vigorously stirred and heated to reflux, slowly Add a mixture of N-bromosuccinimide (35.60 g, 0.2 mol) and benzoyl peroxide (0.36 g, 1.5 mmol). After the addition is complete, continue the reaction for 3 h, cool to room temperature, and remove the formed butyl Diimide, add water to wash the filtrate, wash the organic layer with sodium bicarbonate solution, sodium chloride solution, dry with anhydrous potassium carbonate, evaporate the solvent by rotary evaporator, and purify the crude product by vacuum distillation to obtain the solid product 2, 3-bis(bromomethyl)thiophene 19.2 g (yield 71%).

[0024] Hexamethylenetetramine (32.66 g, 0.23 mol) was dissolved in 100 mL of chloroform, and 2,3-bis(bromomethyl)thiophene (27 g, 0.1 mol) was slowly added dropwise under vigorous stirring. Heat spontaneously to reflux, heat to reflux for 30 min when the re...

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Abstract

The invention discloses a preparation method of 2, 3-thiophenedicarboxaldehyde and belongs to the field of organic synthesis. The preparation method is characterized in that 2, 3-thiophenedicarboxaldehyde as a raw material and N-bromosuccinimide undergo a bromination reaction in the presence of benzoyl peroxide as a catalyst and carbon tetrachloride or trichloromethane as a solvent at a certain temperature to produce 2, 3-di(bromomethyl)thiophene; and 2, 3-di(bromomethyl)thiophene and hexamethylenetetramine undergo a Sommelet reaction in the presence of trichloromethane as a solvent at a certain temperature to produce 2, 3-thiophenedicarboxaldehyde. Compared with the prior art, the preparation method has the advantages that raw materials are cheap and easily available; reaction conditions are mild and can be controlled easily; and a product yield is high.

Description

technical field [0001] The invention relates to a production method of chemical products, in particular to a production method of 2,3-dialdehyde thiophene, belonging to the field of organic synthesis. Background technique [0002] Thiophene has good reactivity and can undergo nitration, sulfonation, alkylation, acylation and halogenation reactions. Thiophene derivatives are widely used in medicine, pesticides, dyes, polymer additives and other fields. In medicine, antibiotic phenyl homologues with thiophene rings have better efficacy, and some new anti-inflammatory and analgesic drugs such as para-hydroxyephedrine and sufentanil are all thiophene derivatives; in addition, in other fine chemical fields, It also has a wide range of applications, and can be used as a fluorescent whitening agent for plastics, injection molding materials, EVA foam and rubber products, synthetic fibers, and coatings. [0003] 2,3-Dialdehyde thiophene (2,3-Thiophenedicarboxaldehyde), also known as...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/22
Inventor 李江涛杨振强王福玲杨瑞娜蒋卫鹏屈凤波崔富民
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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