Preparation method for hypophosphorous acid / phosphorous acid/ phosphate compounds by adopting P(O)-OH-contained compounds

A phosphate ester, phosphinic acid technology, applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic chemistry, etc., can solve the problems of harsh reaction conditions, cumbersome experimental steps, environmental pollution, etc. To achieve the effect of simple preparation, simple and easy method, and high yield

Active Publication Date: 2014-08-13
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods generally adopt air-sensitive reagents (carbon tetrachloride, sulfonyl chloride, etc.), and the experimental steps are loaded down with trivial details, reaction conditions are harsh, the yield is low, and the pollution to the environment is relatively large.

Method used

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  • Preparation method for hypophosphorous acid / phosphorous acid/ phosphate compounds by adopting P(O)-OH-contained compounds
  • Preparation method for hypophosphorous acid / phosphorous acid/ phosphate compounds by adopting P(O)-OH-contained compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 218mg (1.0mmol) of diphenylphosphoric acid, 171ul (1.0mmol) of benzyl bromide and 652mg (2.0mmol) of cesium carbonate into the Schlenk tube under nitrogen atmosphere, and add 3.0ml of organic solvent (tetrahydrofuran, tetrahydrofuran, Diethyl ether, toluene, 1,4-dioxane, N,N-dimethylformamide, dimethyl sulfoxide, acetonitrile), stirred and reacted at 100°C for 12 hours. Through GC detection and analysis, when acetonitrile is used as the reaction solvent, the yield of the coupling reaction can reach 99% yield.

Embodiment 2

[0026] Mix 218mg (1.0mmol) of diphenylphosphoric acid, 171ul (1.0mmol) of benzyl bromide and 2.0mmol of base (triethylamine, sodium bicarbonate, potassium carbonate, sodium carbonate, cesium carbonate, potassium phosphate) under nitrogen atmosphere Added to Schlenk tube, at N 2 3.0 ml of acetonitrile was added under ambient conditions, and the reaction was stirred at 100° C. for 12 hours. Through GC detection and analysis, under the catalysis of 2.0 equivalents of cesium carbonate, the coupling reaction can reach a yield of 99%.

Embodiment 3

[0028] Add 218mg (1.0mmol) of diphenylphosphoric acid, 171ul (1.0mmol) of benzyl bromide and cesium carbonate (1.0mmol, 1.5mmol, 2mmol) into the Schlenk tube under nitrogen atmosphere, and add 3.0ml of acetonitrile under nitrogen atmosphere , The reaction was stirred at 100° C. for 12 hours. Through GC detection and analysis, under the catalysis of 2.0 equivalents of cesium carbonate, the coupling reaction can reach a yield of 99%.

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Abstract

The present invention provides a highly selective synthesis method for hypophosphorous acid / phosphorous acid / phosphate derivatives containing different substituted functional groups. In the present invention, base is adopted as a catalyst, compounds containing P(O)-OH and halogenated aliphatic hydrocarbons are adopted as reaction substrates, and an organic solvent is added into the reaction system. The method has advantages that the catalyst is cheap and easily obtained; reaction conditions are mild, safe and reliable; the selectivity of target product is close to 100%, and the yield is up to 90%. According to the present invention, the problems of low reaction selectivity, tedious reaction steps, low yields, needing reagents harmful to environment and the like in conventional methods for synthesizing hypophosphorous acid / phosphorous acid / phosphate compound are solved. The method has good industrial application prospects. The present invention also provides the corresponding hypophosphorous acid / phosphorous acid / phosphate derivatives containing different substituted functional groups.

Description

【Technical field】 [0001] The invention relates to the field of catalytic synthesis of organic phosphine compounds, in particular to a method for preparing phosphinic acid / phosphinic acid / phosphoric acid ester derivatives from compounds containing P(O)-OH. 【Background technique】 [0002] Organic phosphinic acid / phosphonous acid / phosphoric acid ester compounds are an important class of organic compounds, which have good catalytic activity, optical activity and biological activity, making them useful in biology, medicine, optical active materials and asymmetric Catalytic synthesis and other aspects have a wide range of applications. However, it is difficult to find pure natural organic phosphinic acid / phosphinic acid / phosphate compounds in nature, and most of the phosphorus elements exist in nature in the form of inorganic salts. Acid / phosphate compounds are mostly synthesized by chemical methods. [0003] In recent years, with the continuous expansion of the application fiel...

Claims

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Application Information

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IPC IPC(8): C07F9/12C07F9/32C07F9/11C07F9/48
CPCC07F9/11C07F9/12C07F9/32C07F9/48
Inventor 尹双凤熊碧权周永波韩立彪
Owner HUNAN UNIV
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