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Method for synthesizing end alkynyl by utilizing 1,1-two bromination vinyl compound

A technology of vinyl compounds and compounds, applied in the direction of preparing amino compounds from amines, organic chemical methods, chemical instruments and methods, etc., can solve the problems that the terminal alkyne compound method is not very convenient and economical, and achieve good substrate applicability, The effect of easy operation

Inactive Publication Date: 2011-04-06
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the previous use of organic bases or Grignard reagents as reaction reagents has limited the application of this type of reaction.
Overall, the current methods for synthesizing terminal alkynes are not very convenient and economical

Method used

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  • Method for synthesizing end alkynyl by utilizing 1,1-two bromination vinyl compound
  • Method for synthesizing end alkynyl by utilizing 1,1-two bromination vinyl compound
  • Method for synthesizing end alkynyl by utilizing 1,1-two bromination vinyl compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment 1: the synthesis of p-methylphenylacetylene

[0018]

[0019] Add 138 mg (0.5 mmol) of p-cresyl dibromide, 406 mg (1.25 mmol) of cesium carbonate, and 5 mL of dimethyl sulfoxide into the reactor, and stir the reaction at 95 ° C for 24 hours. After the reaction is complete, add deionized water to the system , extracted with ether. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product, which was then purified by column chromatography using petroleum ether as the eluent to obtain the desired product as a colorless liquid , 53mg, yield 92%.

[0020] Its NMR data are as follows:

[0021] 1 H-NMR (500MHz, CDCl 3 ): δ 2.34(s, 3H), 3.02(s, 1H), 7.11(d, J = 7.85 Hz, 2H), 7.37(d, J = 8.10 Hz, 2H).

Embodiment 2

[0022] Embodiment 2: the synthesis of p-chlorophenylacetylene

[0023]

[0024] Add 148 mg (0.5 mmol) of p-chlorostyryl dibromide, 207 mg (1.5 mmol) of potassium carbonate, and 5 mL of dimethyl sulfoxide into the reactor, and stir the reaction at 140°C for 12 hours. After the reaction is complete, add deionized water, extracted with ether. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product, which was then purified by column chromatography using petroleum ether as the eluent to obtain the desired product as a light yellow liquid , 60mg, yield 88%.

[0025] Its NMR data are as follows:

[0026] 1 H-NMR (500MHz, CDCl 3 ): δ 3.10(s, 1H), 7.28(d, J = 8.90 Hz, 2H), 7.40(d, J = 8.90 Hz, 2H).

Embodiment 3

[0027] Embodiment 3: the synthesis of phenylacetylene

[0028]

[0029] Add 131mg (0.5mmol) of styryl dibromide, 147mg (1.5mmol) of potassium acetate, 244mg (0.75mmol) of cesium carbonate, and 6mL of N,N-dimethylformamide into the reactor, and stir the reaction at 120°C for 10 After 1 hour, the reaction was complete, and deionized water was added to the system, followed by extraction with ether. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product, which was then purified by column chromatography using petroleum ether as the eluent to obtain the desired product as a colorless liquid , 44mg, yield 87%.

[0030] Its NMR data are as follows:

[0031] 1 H-NMR (500MHz, CDCl 3 ): δ3.06(s, 1H), 7.28-7.34(m, 3H), 7.48-7.50(m, 2H).

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Abstract

The invention belongs to the technical field of organic synthetic intermediates and particularly relates to a method for synthesizing end alkynyl by utilizing 1,1-two bromination vinyl compound. The end alkynyl compound is synthesized by using the 1,1-two bromination vinyl compound as raw materials under the alkali condition. The end alkynyl is an important organic synthetic raw material and an intermediate, and can be widely applied to the synthesis of medicines, agricultural medicines, materials and functional molecules. The invention has the advantages of simple operation, mild condition, high yield and the like, thereby having wide application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis intermediates, and in particular relates to a method for synthesizing terminal alkynes using 1,1-dibromovinyl compounds. Background technique [0002] Terminal alkynes are important intermediates in organic synthesis and are widely used in medicine, pesticides and functional materials (Barry M. Trost, et al. Angew. Chem. Int. Ed. 2009, 48 , 5478-5481.). Terminal alkynes participate in 1, 3-dipolar cycloaddition reactions, also known as "click chemistry", to facilitate the synthesis of various types of 1, 2, 3-triazole compounds, which have been widely used in new drugs, Research and development of pesticides, etc. (Franck Amblard, et al. Chem. Rev. 2009, 109 , 4207-4220.). In addition, polyalkyne compounds prepared by the polymerization reaction of terminal alkynes are also widely used in the production of liquid crystal materials (Chang-Min XING, et al. J. Polym. Sci., Part A: P...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B35/00C07C1/26C07C15/48C07C17/00C07C25/24C07C209/68C07C211/45C07C11/28
Inventor 匡春香赵明
Owner TONGJI UNIV
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