Method for synthesizing alkyne bromoacetate compounds

A technology of alkyne bromoacetate and a synthesis method, which is applied in the field of organic compound synthesis, can solve the problems of narrow substrate expansion, poor chemical selectivity, harsh reaction conditions and the like, achieves environmental friendliness, simplified reaction process and simple operation Effect

Inactive Publication Date: 2019-01-11
ZHEJIANG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In order to solve the problems such as harsh reaction conditions, narrow scope of expanded substrates and poor chemoselectivity in the current method for synthesizing alkyne bromoacetate compounds, the present invention proposes a synthetic method of alkyne bromoacetate compounds

Method used

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  • Method for synthesizing alkyne bromoacetate compounds
  • Method for synthesizing alkyne bromoacetate compounds
  • Method for synthesizing alkyne bromoacetate compounds

Examples

Experimental program
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Embodiment 1

[0028] Add 2mmol (0.2043g) of phenylacetylene and 1.2mmol (0.1428g) of potassium bromide into a 50mL three-necked flask, then add 20mL of acetic acid as a solvent, and then add 0.7g of bromate-intercalated zinc-aluminum hydrotalcite ZnAl-BrO 3 - - LDHs, stirred magnetically at 40°C for 4 hours. After the reaction is over, use a centrifuge at 6000r / min to centrifuge to remove the zinc-aluminum hydrotalcite solid, place the resulting liquid in a separatory funnel, add dichloromethane and deionized water, and extract the organic matter obtained from the reaction into the dichloromethane phase to obtain Column chromatography silica gel was added to the solution, the solvent was distilled off under reduced pressure, and the remaining mixture was separated by column chromatography, using a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 15:1 as the eluent, and the eluted fraction containing the product was collected. solution, and the eluent was evaporated...

Embodiment 2

[0031] Add 2mmol (0.2043g) of phenylacetylene and 1.0mmol (0.1190g) of potassium bromide into a 50mL three-necked flask, then add 16mL of acetic acid as a solvent, and then add 0.6g of bromate-intercalated zinc-aluminum hydrotalcite ZnAl-BrO3 - - LDHs, stirred magnetically at 60°C for 6 hours. After the reaction is over, use a centrifuge at 6000r / min to centrifuge to remove the zinc-aluminum hydrotalcite solid, place the resulting liquid in a separatory funnel, add dichloromethane and deionized water, and extract the organic matter obtained from the reaction into the dichloromethane phase to obtain Column chromatography silica gel was added to the solution, the solvent was distilled off under reduced pressure, and the remaining mixture was separated by column chromatography, using a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 15:1 as the eluent, and the eluted fraction containing the product was collected. solution, and the eluent was evaporated t...

Embodiment 3

[0034] Add 2mmol (0.2043g) of phenylacetylene and 1.6mmol (0.1904g) of potassium bromide into a 50mL three-neck flask, then add 24mL of acetic acid as a solvent, and then add 1.4g of bromate-intercalated zinc-aluminum hydrotalcite ZnAl-BrO 3- - LDHs, stirred magnetically at 30°C for 1 hour. After the reaction is over, use a centrifuge at 6000r / min to centrifuge to remove the zinc-aluminum hydrotalcite solid, place the resulting liquid in a separatory funnel, add dichloromethane and deionized water, and extract the organic matter obtained from the reaction into the dichloromethane phase to obtain Column chromatography silica gel was added to the solution, the solvent was distilled off under reduced pressure, and the remaining mixture was separated by column chromatography, using a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 15:1 as the eluent, and the eluted fraction containing the product was collected. solution, and the eluent was evaporated to r...

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Abstract

The invention discloses a method for synthesizing alkyne bromoacetate compounds. The method comprises the following steps: reacting in an organic solvent at a temperature of 30-60 DEG C for 1-6 hoursby taking phenylacetylene compounds shown as a formula I as raw materials, and taking bromate intercalated Zn-Al hydrotalcite ZnAl-BrO3<->-LDHs and alkali metal bromides as a bromine source, to obtaina reaction solution after reaction completion, and performing after-treatment, thereby obtaining the alkyne bromoacetate compounds shown as a formula II. The acetic acid used in the method disclosedby the invention provides an acidic chemical reaction environment and serves as a nucleophilic reagent for direct addition esterification, and the method belongs to atom economic reactions; the bromine source is simple and readily available, the reaction conditions are mild, and the method is environmentally-friendly and simple in operation. The structural formula is as shown in the specification.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing alkyne bromoacetate compounds. (2) Background technology [0002] Vinyl halides, especially vinyl bromides and iodides, play an important role in the construction of polysubstituted alkenes via transition metal-catalyzed cross-coupling reactions or halogen-metal exchange reactions. Alkyne bromoacetates include enol acetates and the reactivity of the carbon-halogen bond makes them one of the most important building blocks in organic synthesis. Vinyl halides are commonly used in transition metal-catalyzed cross-coupling reactions and halogen-metal exchange reactions, and enol acetates are often used as intermediates in organic synthesis and medicinal chemistry. [0003] At present, the synthesis methods of alkyne bromoacetate compounds reported at home and abroad mainly include the following methods: 1. Utilize the coupling reaction of al...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/04C07C69/157C07C201/12C07C205/42
CPCC07C67/04C07C201/12C07C69/157C07C205/42
Inventor 余琴王力耕冯春
Owner ZHEJIANG UNIV OF TECH
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