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Synthesis method of functionally-substituted dicyanoethylene compounds

A technology of dicyanoethylene and synthesis method, which is applied in the field of chemistry, can solve problems such as complex operation and environmental hazards, and achieve the effects of simple operation, environmental friendliness and wide application range

Active Publication Date: 2017-07-21
UNIVERSITY OF CHINESE ACADEMY OF SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] It can be seen that when synthesizing dicyanoethylene compounds at present, the operation is relatively complicated, and benzyl nitrile / cyanide is usually used as a highly toxic drug, which is harmful to the environment

Method used

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  • Synthesis method of functionally-substituted dicyanoethylene compounds
  • Synthesis method of functionally-substituted dicyanoethylene compounds
  • Synthesis method of functionally-substituted dicyanoethylene compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Embodiment 1: 3,4-dibromo-2, the synthesis of 5-dinitrothiophene

[0074]

[0075] 5g of 3,4-dibromothiophene and 10ml of mixed acid (concentrated H 2 SO 4 and concentrated HNO 3 Volume ratio 1:1) was reacted in 5ml chloroform, the reaction temperature was 50°C, the reaction time was 4h, and 6.9g of the product was obtained, the mixed acid was removed, and recrystallized with dichloromethane and petroleum ether (volume ratio 1:4), the yield was 90 %. 13 C NMR (100 MHz, CDCl 3 ) δ 147.68, 117.51.

Embodiment 2

[0076] Example 2: Synthesis of 2,5-dinitro-3,4-diphenylthiophene

[0077]

[0078] Weigh 0.5g (1.52mmol) of the compound 3,4-dibromo-2,5-dinitrothiophene, 0.75g (6.1mmol) of phenylboronic acid, 0.4g (6.8mmol) of KF and four Put 240 mg of triphenylphosphine palladium in a reaction flask, add 24 ml of toluene, 10 ml of water, and 5 ml of ethanol, and ventilate to make the reaction system an oxygen-free environment. Adjust the temperature to 110°C and react for 24h. After the reaction was completed, it was extracted with ethyl acetate, dried over magnesium sulfate, and petroleum ether and dichloromethane (volume ratio 4:1) were used as eluents to pass through the column. After weighing, 0.36 g of product 2a was obtained with a yield of 72%.

[0079] Product 2a 1 H NMR as figure 1 shown. 1 H NMR (400 MHz, DMSO) δ 7.32-7.23 (m, 2H), 7.20-7.13 (m, 1H).

[0080] Product 2a 13 C NMR such as figure 2 shown. 13 C NMR (100MHz, CDCl 3 ) δ 147.47, 143.07, 130.81, 129.33, 129....

Embodiment 3

[0081] Example 3: Synthesis of 2,5-dinitro-3,4-di-p-tolylthiophene

[0082]

[0083] Weigh 0.5g (1.52mmol) of the compound 3,4-dibromo-2,5-dinitrothiophene obtained in Example 1, 0.83g (6.1mmol) of p-tolylboronic acid, and 0.4g (6.8mmol) of KF Put 240 mg of tetraphenylphosphine palladium in a reaction flask, add 24 ml of toluene, 10 ml of water and 5 ml of ethanol, and ventilate to make the reaction system an oxygen-free environment. Adjust the temperature to 110°C and react for 24h. After the reaction was completed, it was extracted with ethyl acetate, dried over magnesium sulfate, and petroleum ether and dichloromethane (volume ratio 4:1) were used as eluents to pass through the column. After weighing, 0.38 g of product 2b was obtained with a yield of 70%.

[0084] Product 2b 1 H NMR as image 3 shown. 1 H NMR (400 MHz, CDCl 3 ) δ 7.06 (d, J=7.9Hz, 2H), 6.89 (d, J=8.0Hz, 2H), 2.31 (s, 3H).

[0085] Product 2b 13 C NMR such as Figure 4 shown. 13 C NMR (100 MHz, ...

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Abstract

The invention discloses a synthesis method of functionally-substituted dicyanoethylene compounds. The synthesis method includes: using 2, 5-dinitrothiophene and triphenylphosphine / triethyl phosphate as raw materials; heating for reaction in an organic solvent, wherein reaction temperature is 90-180 DEG C, a reaction formula is shown as follows, and R refers to aromatic-ring substituent group or alkane substituent group. The synthesis method has the advantages that the synthesis method is simple to operate, wide in substrate application range and environment-friendly; the synthesis method has universality in synthesizing aromatic ring substituted dicyanoethylene compounds and alkyl substituted dicyanoethylene compounds.

Description

technical field [0001] The invention relates to a method for synthesizing a compound, in particular to a method for synthesizing a functionalized substituted dicyanoethylene compound, belonging to the technical field of chemistry. Background technique [0002] Functionalized substituted dicyanoethylene compounds are a valuable and important precursor for the synthesis of organic optoelectronic materials, such as red or near-red light materials, phthalocyanines, porphyrazine, etc. Compounds are obtained as starting materials. At the same time, dicyano-stilbene also has interesting application prospects in the field of biomedicine. [0003] The synthesis of dicyanoethylene compounds usually adopts the following synthetic methods: [0004] (1) Phenylacetonitrile containing Br 2 or I 2 An oxidative coupling reaction occurs under the conditions of an alkoxide or hydroxide aqueous solution: [0005] [0006] The synthesis method is extremely sensitive to the reaction condi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/00C07C255/34C07C255/35C07C255/37C07C255/42C07C255/51C07C255/09C07B43/08
CPCC07B43/08C07C253/00C07C255/34C07C255/35C07C255/37C07C255/42C07C255/51C07C255/09
Inventor 齐婷梁春菁
Owner UNIVERSITY OF CHINESE ACADEMY OF SCIENCES
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