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Synthetic method for beta-bromo ether compound

A synthesis method and compound technology, which is applied in the field of synthesis of brominated ether compounds, can solve the problems of high toxicity, heavy pollution, and harsh reaction conditions, and achieve the effects of short reaction time, good yield, and mild reaction conditions

Inactive Publication Date: 2019-08-23
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In order to solve the problems of large pollution, high toxicity and harsh reaction conditions in the synthesis of 2-bromo-1-methoxyindane and 1,2-diphenyl-1-bromo-2-methoxyethane, The invention provides a method for synthesizing β-bromoether compounds with safety, environmental protection and mild reaction conditions

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Add 2mmol (0.232g) of indene and 2mmol (0.174g) of lithium bromide into a 50mL three-necked flask, then add 12mL of methanol, dropwise add 2mol / L hydrochloric acid and stir to dissolve, then add 1.2g of bromate-intercalated zinc aluminum hydrotalcite ZnAl -BrO 3 - - LDHs, stirred magnetically at 25°C for 5 hours, followed by TLC to complete the reaction. 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 petroleum ether and ethyl acetate at a volume ratio of 5:1 as the eluent, and the eluent containing the product was collected. T...

Embodiment 2

[0033]Add 2mmol (0.232g) of indene and 2mmol (0.174g) of lithium bromide into a 50mL three-necked flask, then add 16mL of methanol, dropwise add 2mol / L hydrochloric acid and stir to dissolve, then add 1.2g of bromate-intercalated zinc aluminum hydrotalcite ZnAl -BrO 3 - - LDHs, stirred magnetically at 25°C for 5 hours, followed by TLC to complete the reaction. 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, the remaining mixture was separated by column chromatography, the eluent containing the product was collected, and the solvent was distilled off from the eluent to obtain a pure product with a yield of ...

Embodiment 3

[0036] Add 2mmol (0.232g) of indene and 2mmol (0.174g) of lithium bromide into a 50mL three-necked flask, then add 12mL of methanol, dropwise add 2mol / L hydrochloric acid and stir to dissolve, then add 2g of bromate-intercalated zinc aluminum hydrotalcite ZnAl- BrO 3 - - LDHs, stirred magnetically at 25°C for 5 hours, followed by TLC to complete the reaction. 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, the remaining mixture was separated by column chromatography, and the eluent containing the product was collected, and the solvent was distilled off from the eluent to obtain a pure product with a yield ...

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Abstract

The invention discloses a synthetic method for a beta-bromo ether compound. The method comprises the following steps: respectively with indene and trans-stilbene as raw materials, adding methanol, alkali metal halide and bromate-intercalated zinc-aluminum hydrotalcite into the indene and the trans-stilbene, carrying out uniform mixing, carrying out a reaction under stirring for 1 to 6 hours at 25to 50 DEG C and a normal pressure under the action of inorganic acid, allowing a TLC tracking reaction to be completed so as to obtain a reaction mixed solution, and carrying out post-treatment so asto respectively obtain 2-bromo-1-methoxyindan and 1,2-diphenyl-1-bromo-2-methoxyethane. The synthetic method provided by the invention is safer and more environmentally-friendly by using the bromate-intercalated zinc-aluminum hydrotalcite and the alkali metal bromide, has mild reaction conditions, short reaction time and good yield, is simple and convenient in operation, can control the generationspeed of a halogen source by changing reaction conditions, and has strong controllability.

Description

[0001] (1) Technical field [0002] The present invention relates to a kind of synthetic method of bromoether compound, specifically, relate to the synthetic method of 2-bromo-1 methoxyindane and 1,2-diphenyl-1-bromo-2-methoxyethane method. [0003] (2) Background technology [0004] 2-Bromo-1-methoxyindane and 1,2-diphenyl-1-bromo-2-methoxyethane are widely used in organic synthesis and can be further transformed into other functional groups with high practical value . For example, ninhydrin can be used for the detection of amino acids and the fingerprint identification of public security departments, and 2-bromo-1-indanone is a pharmaceutical intermediate that can be used to synthesize indinavir for the treatment of HIV-1 infection; 1 , 2-Diphenyl-1-bromo-2-methoxyethane is also used as a common intermediate in the synthesis of fluorescent whitening agents, dyes, scintillation reagents, and drugs. [0005] The method for synthesizing 2-bromo-1 methoxyindane mainly contains...

Claims

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Application Information

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IPC IPC(8): C07C43/192C07C43/174C07C41/06C07C41/22C07C41/36
CPCC07C41/06C07C41/22C07C41/36C07C2602/08C07C43/192C07C43/174
Inventor 王力耕张岩冯春余琴
Owner ZHEJIANG UNIV OF TECH
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