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Method for preparing 1,1,4,4-tetrahalogenated-1,3-butadiene derivative by 1,4-dihalogenated-1,4-di(trisilicon methyl radical)-1,3-butadiene derivatives

A technology of trimethylsilyl and butadiene, which is applied in the preparation of halogenated hydrocarbons, chemical instruments and methods, organic chemistry, etc. Simple and easy operation, convenient for industrialization, and the effect of a wide range of applications

Inactive Publication Date: 2008-01-02
厦门康奥克科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] But so far, there are few studies on the synthesis method and reaction properties of tetrahalogenated butadiene. The tetrabromobutadiene derivative shown below (Org. Lett., 2004, 6, 2081) is obtained

Method used

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  • Method for preparing 1,1,4,4-tetrahalogenated-1,3-butadiene derivative by 1,4-dihalogenated-1,4-di(trisilicon methyl radical)-1,3-butadiene derivatives
  • Method for preparing 1,1,4,4-tetrahalogenated-1,3-butadiene derivative by 1,4-dihalogenated-1,4-di(trisilicon methyl radical)-1,3-butadiene derivatives
  • Method for preparing 1,1,4,4-tetrahalogenated-1,3-butadiene derivative by 1,4-dihalogenated-1,4-di(trisilicon methyl radical)-1,3-butadiene derivatives

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Experimental program
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Effect test

Embodiment 1

[0026] One of the I class compounds in the structural formula (R 1 =R 2 =n-Bu): Synthesis of (5Z,6Z)-5,6-bis(dibromomethylene)decane:

[0027] In a 25 ml round bottom flask, dissolve 1 mmol of (5Z,6Z)-5,6-bis[(trimethylsilyl)bromomethylene]decane in 5 ml of dichloromethane solution and cool to - At 78°C, carefully add 3mmol of liquid bromine, and react at this temperature for 2 hours. After rising to room temperature, add 5ml of saturated sodium sulfite aqueous solution and stir for 15 minutes. Wash twice with 10 ml of ether, combine the organic layers, wash with water, and dry over anhydrous magnesium sulfate. After filtering off the desiccant, the organic solution was distilled off under reduced pressure to remove the solvent, and then separated by silica gel column chromatography, using petroleum ether as the eluent. The pure product (5Z, 6Z)-5,6-bis(dibromomethylene)decane 0.440 g (purity>98%, colorless liquid) can be obtained with an isolated yield of 92%. The NMR and...

Embodiment 2

[0029] The second of class I compounds in the structural formula (R 1 =R 2 =n-Bu): Synthesis of (5Z,6Z)-5,6-bis(iodobromomethylene)decane

[0030] In a 25 mL round bottom flask, dissolve 1 mmol of (5Z,6Z)-5,6-bis[1-iodo-1-(trimethylsilyl)methylidene]decane in 8 mL of dichloromethane solution, cooled to -78°C, carefully added 2.5mmol of liquid bromine, and reacted at this temperature for 2 hours, after rising to room temperature, added 5ml of saturated aqueous sodium sulfite solution and stirred for 15 minutes, added 5ml of dichloromethane to the mixed solution and divided solution, and the aqueous layer was washed twice with 10 ml of petroleum ether. The organic layers were combined, washed with water, and dried over anhydrous sodium sulfate. After filtering off the desiccant, the organic solution was distilled off under reduced pressure to remove the solvent, and then separated by silica gel column chromatography, using petroleum ether as the eluent. 0.510 g of pure produ...

Embodiment 3

[0032] Three of I class compounds in the structural formula (R 1 =R 2 =n-Bu): Synthesis of (Z)-5-(iodobromomethylene)-6-(dibromomethylene)decane

[0033]In a 25 ml round bottom flask, 1 mmol of (5Z, 6Z)-5-[1-iodo-1-(trimethylsilyl)methylidene]-6-[1-bromo-1-( Dissolve trimethylsilyl) methylene] decane in 10 ml of dichloromethane solution, cool to -78°C, carefully add 3.5 mmol liquid bromine, and react at this temperature for 3 hours, then add 5 ml after rising to room temperature Saturated sodium sulfite aqueous solution was stirred for 10 minutes, 5 ml of dichloromethane was added to the mixture, and the layers were separated. The aqueous layer was washed twice with 10 ml of n-pentane. The organic layers were combined, washed with water, and dried over anhydrous magnesium sulfate. After filtering off the desiccant, the organic solution was distilled off under normal pressure to remove the solvent, and then separated by silica gel column chromatography, using petroleum ether ...

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Abstract

The invention discloses an all-purpose method to synthesize 1, 1, 4, 4-tetrahalogenated-1, 3-butadiene derivant with multiple substituent groups, which is characterized by the following: reacting easily obtained 1, 4-dihydrogenated-1, 4-di(trimethyl silicon based)-1, 3-butadiene derivant and liquid bromine directly to obtain the product with high-productivity; obtaining the raw material easily; improving separating productivity with wide fitting scale; simplifying the experiment equipment and operation for industrialized manufacturing.

Description

technical field [0001] The invention relates to a general synthesis method of 1,1,4,4-tetrahalogenated-1,3-butadiene derivatives with various substituents, and belongs to the field of organic synthesis intermediates and synthesis of new functional materials. Background technique [0002] 1,1,4,4-Tetrahalo-1,3-butadiene derivatives with various substituents are important intermediates in organic synthesis. Due to the existence of butadiene skeleton, it often shows It is a good method to construct carbocyclic and heterocyclic compounds, and these heterocyclic compounds often have different photoelectric properties, so they have broad application prospects in the field of functional materials. The coupling reaction of butadienyl halides to construct different carbon-carbon bonds has high reaction yield and good selectivity, and it can be embedded into various molecular structures as functional fragments. The existence of multiple halogens, on the one hand, the multiple reactio...

Claims

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Application Information

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IPC IPC(8): C07C21/20C07C17/093
Inventor 席振峰宋志毅张慧君刘光臻王从洋
Owner 厦门康奥克科技有限公司
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