A method for synthesizing β-bromoformate compounds

A technology of ester compounds and compounds, which is applied in the field of synthesis of organic compounds, can solve the problems of environmental pollution costs, high toxicity, and poor stability of bromine sources, and achieve the effects of environmental friendliness, good stability, and simple operation

Active Publication Date: 2020-06-23
ZHEJIANG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In order to solve the problems of poor bromine source stability, high toxicity, environmental pollution and high cost in the current method for synthesizing β-bromoformate compounds, the present invention proposes a preparation method of β-bromoformate compounds. The synthetic method overcomes the shortcoming of prior art

Method used

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  • A method for synthesizing β-bromoformate compounds
  • A method for synthesizing β-bromoformate compounds
  • A method for synthesizing β-bromoformate compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0030]

[0031] Add 2mmol (0.208g) of styrene and 1.8mmol (0.2142g) of potassium bromide into a 50mL three-necked flask, then add 10mL of formic acid as a solvent, and then add 0.8g of bromate-intercalated zinc-aluminum hydrotalcite ZnAl-BrO 3 - - LDHs, stirred magnetically at 40°C for 2 hours. After the reaction, the resulting reaction solution was centrifuged at 6500r / min to remove the zinc-aluminum hydrotalcite solid, the resulting liquid was placed in a separatory funnel, dichloromethane and deionized water were added, and the organic matter obtained from the reaction was extracted into the dichloromethane phase In the obtained solution, column chromatography silica gel was added, and the solvent was distilled off under reduced pressure, and the remaining mixture was separated by column chromatography, and the mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 10:1 was used as the eluent to collect the product containing The eluent was evaporated...

Embodiment 2

[0034]

[0035] Add 2mmol (0.366g) of 4-bromostyrene and 1.8mmol (0.2142g) of potassium bromide into a 50mL three-neck flask, then add 10mL of formic acid as a solvent, and then add 0.8g of bromate-intercalated zinc-aluminum hydrotalcite ZnAl -BrO 3 - - LDHs, stirred magnetically at 50°C for 2 hours. After the reaction, the resulting reaction solution was centrifuged at 6500r / min to remove the zinc-aluminum hydrotalcite solid, the resulting liquid was placed in a separatory funnel, dichloromethane and deionized water were added, and the organic matter obtained from the reaction was extracted into the dichloromethane phase In the obtained solution, column chromatography silica gel was added, and the solvent was distilled off under reduced pressure, and the remaining mixture was separated by column chromatography, and the mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 10:1 was used as the eluent to collect the product containing The eluent was evapo...

Embodiment 3

[0038]

[0039] Add 2mmol (0.277g) of 4-chlorostyrene and 1.8mmol (0.2142g) of potassium bromide into a 50mL three-necked flask, then add 10mL of formic acid as a solvent, and then add 0.8g of bromate-intercalated zinc-aluminum hydrotalcite ZnAl -BrO 3 - - LDHs, stirred magnetically at 50°C for 2 hours. After the reaction, the resulting reaction solution was centrifuged at 6500r / min to remove the zinc-aluminum hydrotalcite solid, the resulting liquid was placed in a separatory funnel, dichloromethane and deionized water were added, and the organic matter obtained from the reaction was extracted into the dichloromethane phase In the obtained solution, column chromatography silica gel was added, and the solvent was distilled off under reduced pressure, and the remaining mixture was separated by column chromatography, and the mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 10:1 was used as the eluent to collect the product containing The eluent was ...

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Abstract

The invention discloses a preparation method of a beta-bromoformate compound represented by the formula II; with styrene compounds represented by the formula I as a raw material, with bromate intercalated zinc-aluminum hydrotalcite ZnAl-BrO3<->-LDHs and alkali metal bromide as bromine sources, the reaction is carried out for 1-4 hours at the temperature of 30-60 DEG C in a formic acid solvent, andthe obtained reaction liquid is post-treated to obtain the beta-bromoformate compound represented by the formula II. According to the synthesis method, the bromine sources have good stability and aresimple and easy to obtain; the solvent provides an acidic chemical reaction environment, and also is used as a nucleophilic reagent for synthesis of the target product, so the preparation method hasthe advantages of mild reaction conditions, environmental friendliness, simple operation and the like.

Description

[0001] (1) Technical field [0002] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing β-bromoformate compounds. [0003] (2) Background technology [0004] β-Bromoformate and its derivatives are important organic compounds that are widely used in medicine, cosmetics, printing, leather and food industries. Among them, β-bromine long-chain fatty acid ester is a high-pressure lubricating oil that can replace ordinary hydraulic oil. At the same time, β-bromoformate and its derivatives are an important class of organic synthesis intermediates. For example, terminal alkenes can be synthesized from β-bromoformate to epoxy compounds with high optical activity. [0005] At present, the synthetic method of the relevant β-bromoformic acid ester of domestic and foreign reports mainly contains following several methods: Synthesis of β-bromoformate compounds from styrene compounds (see de Souza, A.V.A.; Mendonca, G.F.; Bernini,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/04C07C67/287C07C67/29C07C69/63
Inventor 王力耕章华隆余琴
Owner ZHEJIANG UNIV OF TECH
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