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A kind of synthetic method of aryl carbonyl substituted phosphoric acid ester compound

A synthesis method and compound technology, applied in the synthesis of phosphate compounds, the synthesis of aryl carbonyl substituted phosphate compounds, and the field of organic synthesis, can solve the problems of low functional group tolerance, achieve high efficiency, mild reaction conditions, The effect of good industrial application prospects

Active Publication Date: 2017-03-08
中研(江门)科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In a small number of published documents, such compounds still use the general reaction of acid chlorides and alkyl phosphate compounds. This method has many defects, such as low functional group tolerance, carbonyl needs to be pre-existed in among substrates etc.

Method used

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  • A kind of synthetic method of aryl carbonyl substituted phosphoric acid ester compound
  • A kind of synthetic method of aryl carbonyl substituted phosphoric acid ester compound
  • A kind of synthetic method of aryl carbonyl substituted phosphoric acid ester compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]

[0041] Under light-proof and nitrogen atmosphere, add 100mmol of the above formula (I) compound, 60mmol of the above formula (II) compound, 100mmol of formaldehyde, 4mmol catalyst palladium trifluoroacetylacetonate, 6mmol nitrogen-containing organic ligand L1 and 15mmol accelerator (a mixture of 5mmol DDTC silver salt and 10mmol copper trifluoromethanesulfonate), the temperature was raised to 45°C, and the reaction was stirred at this temperature for 7 Hour.

[0042]After the reaction is complete, the reaction system is naturally cooled to room temperature, filtered, and the pH value of the filtrate is adjusted to neutral, then an equal volume ratio mixture of ethyl acetate and saturated saline is added, fully shaken and extracted 2-3 times, and each The separated organic phase is concentrated under reduced pressure to obtain a residue, and then 300-400 mesh silica gel column chromatography (with a volume ratio of 1:3 mixed solvent of acetone and sherwood oil as el...

Embodiment 2

[0046]

[0047] Under light-proof and nitrogen atmosphere, add 100mmol of the above formula (I) compound, 70mmol of the above formula (II) compound, 150mmol of formaldehyde, 6mmol catalyst palladium trifluoroacetylacetonate, 8mmol nitrogen-containing organic ligand L1 and 18mmol accelerator (a mixture of 4.5mmol DDTC silver salt and 13.5mmol copper trifluoromethanesulfonate), heated to 55 ° C, and stirred at this temperature React for 6 hours.

[0048] After the reaction is complete, the reaction system is naturally cooled to room temperature, filtered, and the pH value of the filtrate is adjusted to neutral, then an equal volume ratio mixture of ethyl acetate and saturated saline is added, fully shaken and extracted 2-3 times, and each The separated organic phase is concentrated under reduced pressure to obtain a residue, and then 300-400 mesh silica gel column chromatography (with a volume ratio of 1:3 mixed solvent of acetone and sherwood oil as eluent) to obtain the abo...

Embodiment 3

[0052]

[0053] Under light-proof and nitrogen atmosphere, in an appropriate amount of organic solvent (a mixture of benzene and PEG-200 at a volume ratio of 1:3), add 100mmol of the above formula (I) compound, 80mmol of the above formula (II) compound, 200mmol of formaldehyde ( It is in the form of paraformaldehyde, converted to the formaldehyde content therein), 7mmol catalyst palladium trifluoroacetylacetonate, 10mmol nitrogen-containing organic ligand L1 and 22mmol accelerator (a mixture of 6mmol DDTC silver salt and 16mmol copper trifluoromethanesulfonate ), was warming up to 60°C, and stirred the reaction at this temperature for 4 hours.

[0054] After the reaction is complete, the reaction system is naturally cooled to room temperature, filtered, and the pH value of the filtrate is adjusted to neutral, then an equal volume ratio mixture of ethyl acetate and saturated saline is added, fully shaken and extracted 2-3 times, and each The separated organic phase is concen...

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Abstract

The invention relates to a synthetic method of a compound of aromatic carbonyl substituting phosphoric acid ester, shown as in a following formula (III). The method comprises the step of reacting a compound of a following formula (I), a compound of a following formula (II) and a carbonyl source compound in an organic solvent in a light-proof nitrogen atmosphere in the presence of a catalyst, a nitrogen-containing organic ligand and an accelerant, so as to obtain the compound of the formula (III), wherein R1 is H, C1 to C6 alkyl, C1 to C6 alkoxy, or halogen; R2 is C1 to C6 alkyl. The reaction catalyst, the nitrogen-containing organic ligand, the accelerant and the organic solvent are selected and combined for use, so as to form a reaction system greatly favorable for reaction and achieve the aim of efficiently obtaining the product, the reaction conditions are mild, amplified production is suitable, and the industrial application prospect is good.

Description

technical field [0001] The invention relates to a method for synthesizing phosphate compounds, more particularly to a method for synthesizing arylcarbonyl-substituted phosphate compounds, and belongs to the field of organic synthesis, especially the synthesis of pharmaceutical intermediates. Background technique [0002] So far, in the technical field of organic chemical synthesis, although there have been many reports on the synthesis methods of phosphate ester compounds, there are few publications on the synthesis process of aryl carbonyl substituted phosphate ester compounds. [0003] In a small number of published documents, such compounds still use the general reaction of acid chlorides and alkyl phosphate compounds. This method has many defects, such as low functional group tolerance, carbonyl needs to be pre-existed in Among the substrates and so on. [0004] Just because of such defects, therefore, the development of novel and effective synthetic methods of arylcarb...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/40
Inventor 施璐
Owner 中研(江门)科技有限公司