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A new method for preparing diarylmethyl substituted phosphonates

A technology of diarylmethyl and arylmethylene is applied in the field of applied catalytic synthesis of organophosphorus compounds, and can solve the problems of harsh reaction conditions, problems of raw material quality, safety, stability and purity, and difficult synthesis techniques, etc. To achieve the effect of mild and easy control of the reaction process, good industrial application prospects, and cheap and easy-to-obtain catalysts

Active Publication Date: 2022-07-12
HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above methods generally use air-sensitive reagents (phosphoryl chloride, etc.), special ligands (ferrocene ligands, carbene ligands, etc.), and there are still cumbersome experimental steps, expensive catalysts, and difficult recycling. Harsh conditions, cross-substrate applicability, low yield, and large environmental pollution
[0005] So far, the efficient synthesis of diarylmethyl-substituted organic phosphonate compounds has several aspects, such as raw material quality, production safety (compounds such as phosphorus oxychloride are highly corrosive), and product stability and purity. The difficulty of synthesis technology is quite difficult. At present, only a few companies in the United States, Japan and other countries are producing, while the current situation of my country's high-end organic phosphonate products mainly depends on imports.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 99.6 mg (0.6 mmol) of triethyl phosphite, 147 mg (0.5 mmol) of 4-phenylmethylene-2,6-di-tert-butyl-2,5-cyclohexadien-1-one , 9.7 mg (0.05 mmol) of silver tetrafluoroborate were added to a Schlenk tube under nitrogen, and 1.0 mL of 1,2-dichloroethane was added under nitrogen. o C stirred the reaction for 3 hours. After the reaction was completed, the yield of the target product was 98% after separation and purification by column chromatography.

Embodiment 2

[0025] 99.6 mg (0.6 mmol) of triethyl phosphite, 154 mg (0.5 mmol) of 4-(4-methylphenyl)methylene-2,6-di-tert-butyl-2,5-cyclohexyl Dien-1-one, 9.7 mg (0.05 mmol) silver tetrafluoroborate were added to a Schlenk tube under nitrogen, 1.0 mL of 1,2-dichloroethane was added under nitrogen, and the mixture was heated to 80 o C stirred the reaction for 3 hours. After the reaction was completed, the yield of the target product was 92% after separation and purification by column chromatography.

Embodiment 3

[0027] 99.6 mg (0.6 mmol) of triethyl phosphite, 175 mg (0.5 mmol) of 4-(4-tert-butylphenyl)methylene-2,6-di-tert-butyl-2,5-cyclo Hexadien-1-one, 9.7 mg (0.05 mmol) silver tetrafluoroborate were added to a Schlenk tube under nitrogen, 1.0 mL of 1,2-dichloroethane was added under nitrogen, and the mixture was heated to 80 o C stirred the reaction for 3 hours. After the reaction was completed, the yield of the target product was 94% after separation and purification by column chromatography.

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Abstract

The invention provides a method for synthesizing diarylmethylphosphonate derivatives containing different substituted functional groups with high efficiency and high selectivity. The method adopts silver tetrafluoroborate as a catalyst, and uses trialkyl phosphite and 4- Arylmethylene-2,6-di-tert-butyl-2,5-cyclohexadiene-1-ketone compounds are used as reaction substrates, and an organic solvent is added to the reaction system. The advantages of this method are as follows: the catalyst is cheap and easy to obtain; the substrate has high applicability; the reaction conditions are mild, safe and reliable; the selectivity of the obtained target product is close to 100%, and the yield is as high as 90%. The method solves the shortcomings of traditional synthesis of diarylmethyl substituted phosphonate derivatives, such as poor reaction selectivity, cumbersome reaction steps, low yield and the need to use environmentally harmful reagents, and has good industrial application prospects. The present invention also provides corresponding diarylmethyl substituted phosphonate derivatives with different substituted functional groups.

Description

technical field [0001] The invention relates to the field of application catalysis synthesis of organophosphorus compounds, in particular to a kind of compound based on trialkyl phosphite and 4-arylmethylene-2,6-di-tert-butyl-2,5-cyclohexanediol The invention discloses a preparation method for preparing diarylmethyl substituted phosphonate derivatives by efficient reaction of alken-1-one compounds. Background technique [0002] Diarylmethyl substituted organophosphonates are an important class of intermediates in organic synthesis. They are widely used in the preparation of pharmaceutical structural substances, optoelectronic materials, efficient flame retardants, and catalyst ligands. [0003] In the process of phosphorylation, tri-coordinate phosphorus reagents are finally converted into tetra-coordinate phosphorus compounds, especially tetra-coordinate phosphorus compounds containing high-energy phosphoryl groups (P=O). In the reaction process of tri-coordinate phosphor...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/40
CPCC07F9/4056C07F9/4075Y02P20/584
Inventor 熊碧权许世攀
Owner HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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