A method for preparing organic phosphate compounds with p(o)-oh compound and aromatic hydrocarbon containing methyl substitution

A technology of methyl aromatic hydrocarbons and organophosphoric acid, applied in organic chemistry, chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, etc., can solve the problems of cross-substrate applicability, cumbersome experimental steps, and harsh reaction conditions etc. to achieve high selectivity, simple method, and simple preparation

Active Publication Date: 2020-07-21
HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

However, the above-mentioned methods generally use air-sensitive reagents (P(O)-H compounds, carbon tetrachloride, sulfuryl chloride, etc.), and there are also problems such as cumbersome experimental steps, expensive catalysts and difficult recycling, harsh reaction conditions, Defects such as cross-substrate applicability, low yield, and large environmental pollution

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 109 mg (0.5 mmol) of diphenylphosphoric acid, 105.7 uL (1 mmol) of toluene, 0.1 mmol of catalyst (tetrabutylammonium iodide, tetrabutylammonium bromide, 18-crown-6-ether, iodine ) and 200uL (1.5 mmol) tert-butyl hydroperoxide were added to the Schlenk tube under the air environment, and 0.5 mL toluene was added under the air condition, at 80 o C stirred the reaction for 12 hours. Through GC detection and analysis, when toluene is used as the reaction solvent and only tetrabutylammonium iodide is used as the catalyst, the yield of the crosslinking reaction can reach 67% yield.

Embodiment 2

[0030] Add 109 mg (0.5 mmol) of diphenylphosphoric acid, 105.7 uL (1 mmol) of toluene, 18.5 mg

[0031] (0.1 mmol) tetrabutylammonium iodide and 1.0 mmol oxidant (tert-butyl hydroperoxide, potassium persulfate, hydrogen peroxide, tert-butyl peroxybenzoate, m-chloroperoxybenzoic acid, di-tert-butyl Peroxide, potassium monopersulfate) was added to the Schlenk tube under the air environment, and 0.5 mL of organic solvent toluene was added under the air environment, at 80 o C stirred the reaction for 12 hours. Through GC detection and analysis, when toluene is used as the reaction solvent and only tert-butyl hydroperoxide is used as the oxidant, the yield of the crosslinking reaction can reach 67% yield.

Embodiment 3

[0033]Mix 109 mg (0.5 mmol) of diphenylphosphoric acid, 105.7 uL (1 mmol) of toluene, 18.5 mg (0.1 mmol) of tetrabutylammonium iodide with different molar ratios of tert-butyl hydroperoxide (2.0-6.0 times) into the Schlenk tube under the air environment, add 0.5 mL organic solvent toluene under the air environment, at 25~80 o C stirred the reaction for 12 hours. Through GC detection and analysis, when toluene is used as the reaction solvent, when the consumption of tert-butyl hydroperoxide is 3 times, the yield of the crosslinking reaction can reach 76% yield.

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Abstract

The invention provides a high-efficiency and high-selectivity synthetic method for organic phosphate derivatives containing different substituted functional groups. The method uses tetrabutylammoniumiodide as a catalyst and uses a P(O)-OH-containing compound and a methyl-containing aromatic hydrocarbon compound as reaction substrates, and an organic solvent and an oxidant are added in the reaction system. The method has the advantages that the catalyst is cheap and easy to obtain, the substrate applicability is high, the reaction conditions are mild, safe and reliable, the selectivity of an obtained target product is close to 100%, and the yield is up to 90% or more. The method solves shortages in traditional organic phosphate ester compound synthetic methods that reaction selectivity ispoor, reaction steps are complicated, the yield is low, environmentally-harmful agents are used and the like, and has better industrial application prospects. The invention also provides the corresponding organic phosphate derivatives containing the different substituted functional groups.

Description

technical field [0001] The invention relates to the field of catalytic synthesis of organic phosphate compounds, in particular to a method for preparing organic phosphate derivatives by efficient oxidative dehydrogenation coupling of P(O)-OH compounds and methyl-containing aromatic hydrocarbon compounds. method of preparation. 【Background technique】 [0002] Organophosphorus compounds are important intermediates in organic synthesis. They are widely used in the preparation of pharmaceutical structural substances, polymer intermediates, photoelectric materials, flame retardants, and lubricants. At the same time, among various organophosphorus compounds with different coordination, the research on one, two and six coordination compounds is the latest work, and they are not yet mature as organic synthesis reagents. Therefore, organophosphorus reagents are currently mainly limited to three-, four-, and five-coordinate phosphorus compounds, especially three-four coordination co...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/32
Inventor 熊碧权王刚唐课文张盼良刘宇许卫风
Owner HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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