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Preparation method of 3-(bromophenyl)-2,2'-difluoropropanoic acid

A technology of difluoropropionic acid and ethyl difluoropropionate, which is applied in the field of preparation of 3--2,2'-difluoropropionic acid, can solve the problems of harsh reaction conditions, difficult industrialized production, complicated operation, etc. The raw materials are easy to obtain, easy to operate, and the raw materials are cheap.

Inactive Publication Date: 2015-04-29
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to solve the existing β, β-difluoro-α-carbonyl aryl derivatives preparation method has many steps, harsh reaction conditions, low yield, complex operation, difficult to be used in industrial production and other deficiencies, to provide A preparation method of 3-(bromophenyl)-2,2'-difluoropropionic acid with simple process, low cost and easy industrialization

Method used

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  • Preparation method of 3-(bromophenyl)-2,2'-difluoropropanoic acid
  • Preparation method of 3-(bromophenyl)-2,2'-difluoropropanoic acid
  • Preparation method of 3-(bromophenyl)-2,2'-difluoropropanoic acid

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Embodiment 1

[0024] A kind of preparation method of 3-(4'-bromophenyl)-2,2'-difluoropropionic acid, comprises the steps:

[0025] 1) Under the protection of nitrogen, add 50mL of anhydrous THF and 0.78g of activated zinc powder (12.0mmol) to a 100mL three-necked flask equipped with a magnetic stirrer. Ethyl difluoroacetate (12.0 mmol) was slowly dropped into the mixed solution, keeping the temperature of the reaction system at 55°C. After the dropwise addition, continue stirring for 5-10 minutes, then add 1.85 g of p-bromobenzaldehyde (10.0 mmol) into the above mixture, and heat to reflux for 2 hours. After the reaction was completed, the reaction liquid was cooled to room temperature, and the pH value of the solution was adjusted to 4-6 with dilute hydrochloric acid, extracted 3 times with ethyl acetate (3×100mL), the organic phases were combined, washed with saturated brine, anhydrous sodium sulfate After drying, spin off the solvent under reduced pressure to obtain 1.85 g of yellow oil...

Embodiment 2

[0030] 1) Under nitrogen protection, add 50 mL of anhydrous THF and 0.98 g of activated zinc powder (15.0 mmol) into a 100 mL three-neck flask equipped with a magnetic stirrer. After the addition, the mixed system was heated to 65°C, and 3.05 g of ethyl bromodifluoroacetate (15.0 mmol) was slowly dropped into the mixed solution, keeping the temperature of the reaction system at 65°C. After the dropwise addition was completed, the stirring reaction was continued for 5-10 min, and then 1.85 g of p-bromobenzaldehyde (10.0 mmol) was heated under reflux for 3 h. After the reaction was completed, the reaction liquid was cooled to room temperature, and the pH value of the solution was adjusted to 4-6 with dilute hydrochloric acid, extracted 3 times with ethyl acetate (3×100mL), the organic phases were combined, washed with saturated brine, anhydrous sodium sulfate After drying, spin off the solvent to obtain 2.24 g of yellow oily product 3-(4'-bromophenyl)-2,2'-difluoro-3-hydroxyprop...

Embodiment 3

[0035] 1) Under nitrogen protection, add 50 mL of anhydrous THF and 1.3 g of activated zinc powder (20.0 mmol) into a 100 mL three-neck flask equipped with a magnetic stirrer. After the addition, the mixed system was heated to 70°C, and 3.05 g of ethyl bromodifluoroacetate (15.0 mmol) was slowly dropped into the mixed solution, keeping the temperature of the reaction system at 70°C. After the dropwise addition was completed, the stirring reaction was continued for 5-10 min, and then 1.85 g of p-bromobenzaldehyde (10.0 mmol) was heated under reflux for 5 h. After the reaction was completed, the reaction liquid was cooled to room temperature, and the pH value of the solution was adjusted to 4-6 with dilute hydrochloric acid, extracted 3 times with ethyl acetate (3×100mL), the organic phases were combined, washed with saturated brine, anhydrous sodium sulfate After drying, spin off the solvent to obtain 2.45 g of yellow oily product 3-(4'-bromophenyl)-2,2'-difluoro-3-hydroxypropi...

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Abstract

The invention provides a preparation method of 3-(bromophenyl)-2,2'-difluoropropanoic acid. Specifically, bromobenzaldehyde serving as a raw material and ethyl bromodifluoroacetate undergo addition reaction to obtain 3-(bromophenyl)-2,2'-difluoro-3-ethyl hydroxyropanoate; the 3-(bromophenyl)-2,2'-difluoro-3-ethyl hydroxyropanoate is subjected to bromo-substitution to obtain 3-(bromophenyl)-2,2'-difluoro-3-ethyl bromopropionate; and the 3-(bromophenyl)-2,2'-difluoro-3-ethyl bromopropionate is subjected to hydroxy reduction and hydrolytic degreasing reaction to obtain the 3-(bromophenyl)-2,2'-difluoropropanoic acid. The preparation method is simple in synthetic route, easy to operate, cheap and readily available in raw materials and mild in reaction condition, the intermediate and the product are easy to separate, and the yield is relatively high, so the preparation method is suitable for industrialized production. The prepared 3-(bromophenyl)-2,2'-difluoropropanoic acid has a wide application value in a beta-oxidation process inhibitor in pest control and pheromone bio-synthesis.

Description

technical field [0001] The invention relates to fluorocarbonyl derivatives, in particular to a preparation method of 3-(bromophenyl)-2,2'-difluoropropionic acid. Background technique [0002] The introduction of fluorine atoms into specific positions of bioorganic molecules will lead to significant changes in their stability, lipophilicity and biological activity. These apparent changes originate from the high electronegativity of the fluorine atom, the strong carbon-fluorine bond, and the similar size of the halogens and hydrogen. In the past decade, fluorine compounds have been widely used in the fields of medicine, agricultural chemistry and biology. due to CF 2 The substitution of / O has isoelectronic and isosteric properties, and many biologically active natural product substitutes have been prepared, such as fluorinated antibacterial agents and enzyme inhibitors. In addition, the use of organofluorine compounds can serve as new tools to provide new research strate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C57/58C07C51/02
CPCC07C51/09C07C67/307C07C67/317C07C67/343C07C57/58C07C69/732C07C69/65
Inventor 王晓菊魏超飞冯丽恒
Owner SHANXI UNIV
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