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Method for preparing formyl aryl phosphonate by dehydrocoupling aromatic aldehyde and h-phosphonate

A technology of formyl aryl phosphonate and dehydrogenation coupling, applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic chemistry, etc., to achieve good tolerance, wide application range, avoid Effect of the prefunctionalization step

Inactive Publication Date: 2016-09-14
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The corresponding formyl aryl phosphonates are prepared by dehydrogenation cross-coupling reaction between the carbon-hydrogen bond of aromatic aldehyde and the phosphorus-hydrogen bond of dialkyl H-phosphonate, which has not been reported yet.

Method used

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  • Method for preparing formyl aryl phosphonate by dehydrocoupling aromatic aldehyde and h-phosphonate
  • Method for preparing formyl aryl phosphonate by dehydrocoupling aromatic aldehyde and h-phosphonate
  • Method for preparing formyl aryl phosphonate by dehydrocoupling aromatic aldehyde and h-phosphonate

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Embodiment 1

[0028] The reaction raw materials listed in Table 1 are prepared in the following steps:

[0029] Ag 2 O (5.8mg, 0.025mmol, 5mol%) and K 2 S 2 o 8 (270mg, 1.0mmol, 2equiv) dissolved in CH 3 CN / H 2 O (2.5mL / 2.5mL) mixed solution 5ml, then added to the mixed solution of dialkylphosphonate 2a-b (1.0mmol) and aromatic aldehyde 1a-i (0.5mmol). The reaction mixture was stirred at 100°C for 1.5 hours.

[0030] Filter the reaction product to obtain the filtrate and filter residue respectively; wash the filter residue with ethyl acetate (5mL×2) to obtain the washing solution;

[0031] The filtrate and washings were combined and concentrated (i.e., rotovaped off the solvent, which included CH 3 CN, H 2 (2, ethyl acetate), the resulting concentrate was separated by column chromatography (silica gel, petroleum ether / ethyl acetate as eluent) to obtain formyl aryl phosphonate (3).

[0032] The column chromatography separation of 10 kinds of formyl aryl phosphonates is specifically ...

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Abstract

The invention discloses a method for preparing formylaryl phosphonate by dehydrogenation coupling of aromatic aldehyde and H-phosphonate. The method comprises the following steps: dissolving Ag2O and K2S2O8 in a mixed solution of CH3CN / H2O, adding to a mixed solution of dialkyl phosphonate and aromatic aldehyde, and reacting under stirring for 1.5 hours at 95-105 DEG C to obtain a reactant, wherein the molar ratio of dialkyl phosphonate to aromatic aldehyde is (1.8-2.2): 1, the molar ratio of Ag2O to aromatic aldehyde is 4.5%-5.5% and the molar ratio of K2S2O8 to aromatic aldehyde is (1.8-2.2): 1; filtering the reactant to obtain a filtrate and filter residue; washing the filter residue with ethyl acetate to obtain a washing liquid; mixing the filtrate and the washing liquid, concentrating to obtain a concentrate and separating the concentrate by column chromatography to obtain formylaryl phosphonate.

Description

technical field [0001] The invention relates to a method for preparing formyl aryl phosphonate through the dehydrogenative cross-coupling reaction of aromatic aldehyde derivatives and dialkyl phosphonate. Background technique [0002] Many aryl phosphonate derivatives have important physiological activities and are used in drug candidates or medicines. Among the many synthetic methods for obtaining aryl phosphonates, the most commonly used and more traditional method is: coupling aromatic hydrocarbons with easily leaving functional groups with dialkyl H-phosphates. However, compared with the direct use of the dehydrogenation cross-coupling reaction between the carbon-hydrogen bonds of arene derivatives and the phosphorus-hydrogen bonds of dialkyl H-phosphates, such traditional methods require prefunctionalization of aromatic rings. , thereby increasing the reaction and separation steps, thereby increasing production costs and environmental pollution. [0003] For example, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/40
Inventor 黄志真黄杏芬何牮石吴清来
Owner ZHEJIANG UNIV