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4-bromobenzo [1, 2-b: 3, 4-b] dithiophene-2, 7-diformaldehyde and preparation method thereof

A technology of nitroisophthalaldehyde, 2-b, applied in chemical instruments and methods, preparation of nitro compounds, preparation of organic compounds, etc., can solve the problems of low yield, many reaction steps, high temperature requirements and the like, Achieve the effect of easy availability of raw materials, easy reaction and simple synthesis process

Pending Publication Date: 2022-05-31
QINGDAO AGRI UNIV
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  • Claims
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Problems solved by technology

Moreover, regarding the synthesis of benzodithiophene compounds, the current method mainly utilizes organic sulfur sources with strong odor and easy oxidation, and uses transition metals as catalysts to catalyze the formation of C-S bonds, cyclization to form thiophene ring skeletons, and the reaction The process has high requirements on reaction conditions such as temperature and catalyst, and there are many reaction steps and low yield

Method used

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  • 4-bromobenzo [1, 2-b: 3, 4-b] dithiophene-2, 7-diformaldehyde and preparation method thereof
  • 4-bromobenzo [1, 2-b: 3, 4-b] dithiophene-2, 7-diformaldehyde and preparation method thereof
  • 4-bromobenzo [1, 2-b: 3, 4-b] dithiophene-2, 7-diformaldehyde and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The preparation of 4-bromobenzo[1,2-b:3,4-b']dithiophene-2,7-dicarbaldehyde is as follows:

[0033] Add 506mg of 4,6-dibromo-2-nitroisophthalaldehyde (1.5mmol) and 256mg 2,5-dihydroxy-1,4-dithiane (1.65mmol) into a 50mL three-necked flask, add Stir N,N-dimethylformamide (DMF) to dissolve the raw materials, then add 0.9mL triethylamine (6mmol), heat in an oil bath, keep the temperature at 35°C, react for 8h, cool to room temperature naturally, add a certain amount ice water, centrifuged, washed with distilled water and tetrahydrofuran in sequence, and the obtained product was vacuum-dried at 60°C to obtain 4-bromobenzo[1,2-b:3,4-b']dithiophene- 2,7-Dicarbaldehyde, yield 79.6%.

[0034] The NMR data of 4-bromobenzo[1,2-b:3,4-b']dithiophene-2,7-dicarbaldehyde are as follows:

[0035] 1 H NMR (500MHz, DMSO-d6): δ=10.24(s,1H,-CHO),10.18(s,1H,-CHO),8.84(s,1H,

[0036] -PhH), 8.63(s,1H,thiohene-H),8.61(s,1H,thiohene-H). 13 C NMR (126MHz, DMSO-d6): δ = 119.02, 124.69, 133.11...

Embodiment 2

[0038] The preparation of 4-bromobenzo[1,2-b:3,4-b']dithiophene-2,7-dicarbaldehyde is as follows:

[0039] Add 506mg of 4,6-dibromo-2-nitroisophthalaldehyde (1.5mmol) and 256mg 2,5-dihydroxy-1,4-dithiane (1.65mmol) into a 50mL three-necked flask, add Stir N,N-dimethylformamide (DMF) to dissolve the raw materials, then add 1.13mL triethylamine (7.5mmol), heat in an oil bath, keep the temperature at 35°C, react for 7h, cool to room temperature naturally, add certain amount of ice water, centrifuged, and the product was washed with distilled water and tetrahydrofuran in sequence, and the obtained product was vacuum-dried at 60°C to obtain 4-bromobenzo[1,2-b:3,4-b']dithiophene -2,7-Dicarbaldehyde, yield 75.4%.

Embodiment 3

[0041] The preparation of 4-bromobenzo[1,2-b:3,4-b']dithiophene-2,7-dicarbaldehyde is as follows:

[0042] Add 506mg of 4,6-dibromo-2-nitroisophthalaldehyde (1.5mmol) and 256mg 2,5-dihydroxy-1,4-dithiane (1.65mmol) into a 50mL three-necked flask, add Stir tetrahydrofuran (THF) to dissolve the raw materials, then add 1.13mL triethylamine (7.5mmol), heat in an oil bath, keep the temperature at 50°C, react for 9h, cool to room temperature naturally, add a certain amount of ice water, centrifuge, and use The product was washed sequentially with distilled water and tetrahydrofuran, and the obtained product was vacuum-dried at 60°C to obtain 4-bromobenzo[1,2-b:3,4-b']dithiophene-2,7-dicarbaldehyde, Yield 70.9%.

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Abstract

The invention discloses 4-bromobenzo [1, 2-b: 3, 4-b '] dithiophene-2, 7-diformaldehyde and a preparation method thereof, and belongs to the technical field of organic synthesis. The 4-bromobenzo [1, 2-b: 3, 4-b '] dithiophene-2, 7-dicarboxaldehyde disclosed by the invention is prepared from 4, 6-dibromo-2-nitroisophthalaldehyde and 2, 5-dihydroxy-1, 4-dithiane, and the structural formula of the 4-bromobenzo [1, 2-b: 3, 4-b'] dithiophene-2, 7-dicarboxaldehyde is shown in the description. Dithiane is used as a sulfur source, mercaptoethanol generated by depolymerization in the presence of alkali is subjected to nucleophilic substitution to complete formation of a C-S bond, the synthesis process is simpler, the reaction conditions are mild and easy to control, the reaction is easy to amplify, the raw materials are simple and easy to obtain, and the safety coefficient is high. As a compound containing a benzodithiophene skeleton, 4-bromobenzo [1, 2-b: 3, 4-b '] dithiophene-2, 7-dicarboxaldehyde can be applied to preparation of energy storage products such as transistors, batteries and supercapacitors, and has a wide application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to 4-bromobenzo[1,2-b:3,4-b']dithiophene-2,7-dicarbaldehyde and a preparation method thereof. Background technique [0002] As an important class of heterocyclic compounds, benzothiophene can be used to construct various functional organic materials with a wide range of applications. Thiophene-based organic π-conjugated oligomers and polymers are playing an increasingly important role in energy storage applications such as organic field-effect transistors, organic solar cells, and supercapacitors. Among these benzothiophene compounds, benzo[1,2-b:5,4b']dithiophene with rigid planar conjugated structure is an important component in the synthesis of thiophene functional organic materials. Moreover, regarding the synthesis of benzodithiophene compounds, the current method mainly utilizes organic sulfur sources with strong odor and easy oxidation, and uses transiti...

Claims

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Application Information

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IPC IPC(8): C07D495/04C07C205/44C07C201/12C07C205/26C07C205/42C07C205/12C07C201/08
CPCC07D495/04C07C201/12C07C201/08C07C205/44C07C205/26C07C205/42C07C205/12Y02E10/549
Inventor 郝龙张建平魏红涛
Owner QINGDAO AGRI UNIV
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