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Preparation method of flocoumafen

A technology of fluocorone and molar ratio, which is applied in the field of synthesis of the second-generation anticoagulant rodenticide, fluocorone, and can solve the problem of difficult to buy, irregular method, and conversion of methoxyphenyl benzyl ketone Low yield and other problems, to achieve the effect of simple and easy reaction, easy post-treatment operation, and increase the overall reaction yield

Inactive Publication Date: 2012-08-01
NANJING UNIV OF SCI & TECH +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The raw material Witting reagent used for the synthesis of fluororaurone in the patent GB2126578 is not easy to buy, and needs to be prepared by itself, which increases the cost
In 2000, the article "Synthesis of Highly Efficient Rodenticide Rodenticide" was improved on the basis of this patent, using ethyl acetate instead of Witting reagent as the starting material, but still using the Grignard reagent of benzyl bromide and carbon carbon The reaction of double bond addition has two difficulties: one is that the Grignard reagent of benzyl bromide is prone to dimerization to generate 1,2-diphenylethane; the other is that the Grignard reagent is a nucleophile, Not easy to attack the carbon-carbon double bond
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Method used

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  • Preparation method of flocoumafen
  • Preparation method of flocoumafen
  • Preparation method of flocoumafen

Examples

Experimental program
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Example Embodiment

[0047] Example 1

[0048] In the first step, 7.725g (0.05mol) of phenylacetyl chloride and 10.08g (0.10mol) of anisole were dissolved in 50mL of dichloromethane, 13.35g (0.10mol) of aluminum trichloride was added at -20°C, and stirred for 16h After the end, the reaction solution was poured into 10% hydrochloric acid, and the phases were separated. The organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain the crude product, which was then recrystallized from methanol to obtain white crystals of 4-methoxybenzene. phenethyl ketone.

[0049] In the second step, 2.26g (0.01mol) of the product of the first step, 0.48g (0.02mol) of magnesium powder, and 1.67g (0.01mol) of ethyl bromoacetate were dissolved in 15mL of benzene, and 0.01 g of ethyl bromoacetate was added dropwise at 25°C under vigorous stirring. mol boron trifluoride·acetonitrile, and stir for 3-4h after the dropwise addition. After th...

Example Embodiment

[0185] Example 2

[0186] The reaction steps are exactly the same as in Example 1, except that:

[0187] For the first step, the anisole was changed to 5.04 g (0.05 mol) and aluminum trichloride was added at 15°C.

[0188] For the second step, 0.56g (0.01mol) iron powder was selected as the metal reagent, tetrahydrofuran was selected as the solvent, 6.68g (0.04mol) of ethyl bromoacetate was selected, and 0.01mol of boron trifluoride·tetrahydrofuran was added dropwise at 35°C.

[0189] For the third step, triethylsilane was changed to 3.48 g (0.03 mol), trifluoroacetic acid was changed to 1.14 g (0.01 mol), and 0.005 mol of boron trifluoride·tetrahydrofuran was used for the boron trifluoride complex.

[0190] For the fourth step, the amount of sodium hydroxide was changed to 3.20 g (0.08 mol), and the recrystallization reagent was methanol.

[0191] For the fifth step, the reaction temperature was 90° C., the amount of PPA was 16.90 g (0.05 mol), and the mixture was stirred...

Example Embodiment

[0197] Example 3

[0198] The reaction steps are exactly the same as in Example 1, except that:

[0199] For the first step, the anisole was changed to 7.56 g (0.075 mol), and 6.625 g (0.05 mol) of aluminum trichloride was added at 0°C.

[0200] For the second step, 2.56g (0.04mol) copper powder was selected as the metal reagent, toluene was selected as the solvent, and ethyl bromoacetate was changed to 3.34g (0.02mol), and 0.02mol boron trifluoride·ether was added dropwise at 55°C.

[0201] For the third step, triethylsilane was changed to 4.64 g (0.04 mol), trifluoroacetic acid was changed to 3.42 g (0.03 mol), and 0.02 mol of boron trifluoride·acetonitrile was used for the boron trifluoride complex.

[0202] For the fourth step, the amount of sodium hydroxide was changed to 1.60 g (0.04 mol), and acetonitrile was selected as the recrystallization reagent.

[0203] For the fifth step, the reaction temperature was 120° C., the amount of PPA was 10.14 g (0.03 mol), and the...

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Abstract

The invention discloses a preparation method of flocoumafen, which treats anisole and phenylacetyl chloride as initial raw materials to sequentially obtain a white crystal 4-methoxyphenylacetophenone, 4-phenyl-3-(4-methoxyphenyl)-3-ethylhydroxybutyrate, 4-phenyl-3-(4-methoxyphenyl)ethyl butyrate, a white solid 4-phenyl-3-(4-methoxyphenyl)butyric acid, a light yellow solid 3-(4-methoxyphenyl)-1-tetralone, 3-(4-methoxyphenyl)-1-tetrahydronaphthol, 4-hydroxy-3-{1,2,3,4-tetrahydro-3-(4-methoxyphenyl)-1-naphthalene}coumarin, 4-hydroxy-3-{1,2,3,4-tetrahydro-3-(4-hydroxyphenyl)-1-naphthalene}coumarin, and 4-hydroxy-3-[1,2,3,4-tetrahydro-3-{4-(4-trifluoromethylbenzyloxy)phenyl}-1-naphthalene]coumarin. The preparation method of the invention has the advantages of cheap and easily available raw materials, simple and easily carried out reactions, and simple post-processing operation; and boron trifluoride is used as a Lewis acid to substitute iodine to solve a problem of low conversion rate formerly existing in a second step of OeeSookPark and BongSuekJang, so the total reaction yield is improved, and the industrial production of flocoumafen has a meaning.

Description

technical field [0001] The invention belongs to the field of fine chemical industry, and specifically relates to the synthesis of a second-generation anticoagulant rodenticide flumarone. Background technique [0002] Flocoumafen, also known as killing it, is a second-generation coumarin anticoagulant patented by Shell in 1984. It is characterized by high efficiency, good palatability, high selective killing, good killing effect on various rodents, including rodents that are resistant to the first generation of anticoagulants, and has Potent antidote vitamin K1. The second-generation anticoagulant represented by fluocorone, which has the advantages of both acute rodenticide and chronic rodenticide, is a new development in the field of rodenticide research and development, and has theoretical and practical significance for the exploration of its preparation method . [0003] At present, there are very few reports on the synthesis of flumarone at home and abroad. In the pat...

Claims

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Application Information

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IPC IPC(8): C07D311/56
Inventor 季红梅蔡春魏晓廷石永飞
Owner NANJING UNIV OF SCI & TECH
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