A method for synthesizing β-haloformate compounds

A technology of ester compounds and haloformic acid, which is applied in the field of synthesis of organic compounds, can solve problems such as high toxicity, environmental pollution costs, and poor stability of halogen sources, and achieve the effects of simple operation, environmental friendliness, and mild reaction conditions

Active Publication Date: 2020-10-09
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] In order to solve the problems of poor halogen source stability, high toxicity, environmental pollution and high cost in the current method for synthesizing β-haloformate compounds, the present invention proposes a preparation method of β-haloformate compounds, Synthetic method of the present invention has overcome the shortcoming of prior art

Method used

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

Examples

Experimental program
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Embodiment 1

[0031]

[0032] Add 2mmol (0.172g) of 3-methyl-2-buten-1-ol 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 The intercalated zinc-aluminum hydrotalcite ZnAl-BrO3--LDHs was magnetically stirred at 40°C for 4 hours. After the reaction is over, use a centrifuge at 6500r / 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 10:1 as the eluent, and the eluted product containing the product was collected. The solvent was disti...

Embodiment 2

[0035]

[0036] Add 2mmol (0.172g) of 3-methyl-2-buten-1-ol and 2.2mmol (0.3652g) of potassium iodide into a 50mL three-necked flask, then add 10mL of formic acid as a solvent, and then add 0.8g of bromate for intercalation ZnAl-BrO 3 -- LDHs, stirred magnetically at 25° C. for 6 hours, followed by TLC to complete the reaction. After the reaction is over, use a centrifuge at 6500r / 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 10:1 as the eluent, and the eluted product containing the product was collected. The...

Embodiment 3

[0039]

[0040] Add 2mmol (0.210g) of 2-vinylpyridine 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- BrO3--LDHs, magnetic stirring at 40°C for 2.5 hours. After the reaction is over, use a centrifuge at 6500r / 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 2:1 as the eluent, and the eluted product containing the product was collected. The solvent was distilled off from ...

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Abstract

The invention discloses a preparation method of a beta-halogenated formic acid ester compound represented by the formula II; with alkene compounds represented by the formula I as raw material, and with bromate intercalated zinc-aluminum hydrotalcite ZnAl-BrO3<->-LDHs and alkali metal halide as halogen sources, the reaction is carried out for 1-4 hours at the temperature of 30-60 DEG C in a formicacid solvent, and the obtained reaction liquid is post-treated to obtain the beta-halogenated formic acid ester compound represented by the formula II. According to the method, the halogen sources have good stability and are simple and easy to obtain; the solvent formic acid provides an acidic chemical reaction environment, also is used as a nucleophilic reagent for synthesis of the target product, and gives full play to acidity, solubility and nucleophilicity, and the reaction process is simplified, so the preparation method has the advantages of high yield, 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-haloformate compounds. [0003] (2) Background technology [0004] β-haloformic acid esters and their derivatives are very useful synthetic intermediates, so they are widely used in medicine, pesticides, cosmetics, printing, leather and food industries, etc. An important structural unit of thermal products and fragrances. For example: due to the low bond energy of the carbon-iodine bond, the structure can undergo a cross-coupling reaction under the catalysis of palladium to increase the carbon chain; of various organic compounds. [0005] At present, the synthetic methods of the relevant β-haloformic acid esters reported at home and abroad mainly contain the following methods: 1. ammonium bromide and potassium persulfate compound salt are combined with benzene in the presence of N,N-dimethylformamide Vinyl compounds synthesize...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B41/12C07C67/04C07C67/287C07C69/63C07D213/30
Inventor 王力耕余琴章华隆
Owner ZHEJIANG UNIV OF TECH
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