Method for manufacturing phosphonate esters

Organic compounds -- part of the class 532-570 series – Organic compounds – Phosphorus esters

Reexamination Certificate

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Reexamination Certificate

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10853312

ABSTRACT:
The present invention relates to a new manufacturing method for phosphonate esters, which have utility as a carbon-carbon binding formation agent, as well as a synthesis intermediate for biologically active substances such as medical drugs and agri-chemicals.Specifically the present invention relates to a new industrially advantageous manufacturing method for phosphonate esters in which the phosphonate esters of the subject can be efficiently obtained with a high yield rate through a simple operation while having barely any side reaction or sub-product.More specifically, the present invention pertains to a manufacturing method for phosphonate esters in which secondary phosphonate esters and alkene compounds are reacted in a transition metal catalyst. In addition the present invention relates to a new manufacturing method for allylphosphonate esters in which secondary cyclic phosphonate esters and 1,3-diene compounds are reacted in a palladium catalyst.

REFERENCES:
patent: 6949667 (2005-09-01), Han et al.
patent: 2322373 (1998-08-01), None
patent: 57-48995 (1982-03-01), None
patent: 2001-247586 (2001-09-01), None
patent: 2001-247586 (2001-09-01), None
Zhao et al, “Palladium-Catalyzed Hydrophosphorylation of Allenes Leading to Regio- and Stereoselective Formation of Allylphosphonates,” Organometallics, vol. 19, p. 4196-4198 (2000).
European Examination Report (Mar. 28, 2003).
Christen, H. R., “Grundlagen der Oranischen Chemie,” pp. 109 & 124, (1982).
Han et al., “High Reactivity of a Five-Membered Cyclic Hydrogen Phosphate,” J. Am. Chemical Society, vol. 122, No. 22, pp. 5407-5408 (2000).
Li-Biao Han et al., “Palladium-catalyzed Hydrophosphorylation of Alkynes via Oxidative Addition of HP(O)(OR)2” Journal of the American Chemical Society, 1996, pp. 1571-1572.
Mirzaei et al., “Palladium-catalyzed Hydrophosphorylation of 1,3-dienes Leading to Allyphosphonates”, Tetrahedron Letters, 2001, pp. 297-299.
Toshikazu Hirao et al., “Palladium-catalyzed New Carbon-Phosphorus Bond Formation,” Bull. Chem. Soc. Jpn., vol. 55, No. 3, pp. 909-913, The Chemical Society of Japan (Mar. 1982).
Xiyan Lu et al., “Nickel Chloride Catalyzed Rearrangement of Allylic Phosphites,” J. Organometallic Chemistry, vol. 304, Nos. 1-2, pp. 239-243, Elsevier Sequoia S.A. (1986).
Chang-Qiu Zhao et al., “Palladium-Catalyzed Hydrophosphorylation of Allenes Leading to Regio- and Stereoselective Formation of Allylphosphonates,” Organometallic, vol. 19, No. 21, pp. 4196-4198, American Chemical Society (Oct. 2000).
Li-Biao Han et al., “High Reactivity of Five-Membered Cyclic Hydrogen Phosphonate Leading to Development of Facile Palladium-Catalyzed Hydrophosphorylation of Alkenes,” 122 J. Am. Chem. Soc.5407-5408 (Jun. 2000).

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