Method for producing 1,2-phenylethane compound using atom...

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

Reexamination Certificate

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Reexamination Certificate

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08034971

ABSTRACT:
An object of the present invention is to provide a method capable of producing a 1,2-phenylethane compound with extremely high yield in a short amount of time. Disclosed is a method for producing a 1,2-phenylethane compound, which comprises subjecting a compound represented by formula (I):wherein Ra represents a hydrogen atom or a substituted or unsubstituted phenyl group; Rb represents a hydrogen atom or a substituent; n represents an integer of 1 to 5 and, when n is 2 or more, Rb may be the same or different, or may be combined with each other to form a ring; and X represents a halogen atom; to a coupling reaction in the presence of a transition metal complex to produce a compound represented by formula (II):

REFERENCES:
patent: 6566548 (2003-05-01), Abe et al.
patent: 1 120 391 (2001-08-01), None
patent: 57-065716 (1982-04-01), None
patent: 07-076538 (1995-03-01), None
patent: WO 2000/023072 (2000-04-01), None
Johnson, David K.; Ciavarri, Jeffrey P.; Ishmael, Faoud T.; Schillinger, Kurt J.; van Geel, Thomas A. P.; Stratton, Stephen M., A novel copper(I) mediated, symmetrical coupling procedure for alkyl, aryl, benzyl, and thiophenyl dihalides, Tetrahedron Letters (1995), 36(47), 8565-8.
Silverman, R., The Organic Chemistry of Drug Design and Drug Action, 1992, Academic Press Inc.
Sayles, D. C.; Kharasch, M. S., The synthesis of symmetrically substituted ethane derivatives, Journal of Organic Chemistry (1961), 26, 4210-14.
Casreact abstract, Accession No. 56:53067, Sayles, D. C.; Kharasch, M. S., The synthesis of symmetrically substituted ethane derivatives, Journal of Organic Chemistry (1961), 26, 4210-14.
Pri-Bar, IIa, Transformation of carbinols by dichlorotris(triphenylphosphine)ruthenium and by some other transition-metal catalysts, Journal of Organic Chemistry (1980), 45(22), 4418-28.
Inductive Effect Printout http://en.wikipedia.org/wiki/Inductive—effect.
Japanese Patent Office, International Search Report (translated) dated May 1, 2007, from related International Patent Application No. PCT/JP2007/055393 , filed on Mar. 16, 2007 (in Japanese).
Japanese Patent Office, International Preliminary Report on Patentability and Written Opinion (translated) dated Oct. 21, 2008, from related International Patent Application No. PCT/JP2007/055393 , filed on Mar. 16, 2007 (in Japanese).
Chwala and Bartek, “Über einige Kondensationsreaktionen des Glyoxals, ” Monatshefte fur Chem I e., 82, 652-655 (1951).
T. Osako et al., “Carbon-Halogen Bond Activation Mechanism by Copper(I) Complexes of (2-Pyridyl)alkylamine Ligands,”Inorg. Chem., 2005, vol. 44, pp. 410-415.
Jean-March Kern et al., “Photoassisted C-C Coupling via Electron Transfer to Benzylic Halides by a Bis(di-imine) Copper(i) Complex,”J. Chem. Soc., Chem. Comm., 1987, pp. 546-548.
Khurana et al., “Facile reductive coupling of benzylic halides with ferrous oxalate dihydrate,”Organic and Biomolecular Chemistry, vol. 1, pp. 1737-1740, 2003.
Li et al., “Ruthenium-catalyzed carbon-carbon formation to synthesize tetraarylethanes and tetraarylxylylene through dechlorinative dimeric reaction,”Journal of Organometallic Chemistry, 687, pp. 12-15, 2003.
Francalanci et al., “Phase-transfer catalysis in cobalt catalyzed carbonylation of secondary benzyl halides,”Journal of Electroanalytical Chemistry, vol. 232, pp. 59-70, 1982.
Whitmore et al., “The reaction of organic mercury compounds with organic halides. II1,”Journal of the American Chemical Society, vol. 51, No. 5, pp. 1491-1503, May 1, 1929.
Li et al., “Ruthenium-catalyzed coupling reaction of benzylic halides,”Synthetic Communications, vol. 33, No. 20, pp. 3583-3588, Oct. 20, 2003.
Liu et al., “Tuning the electrical conductivity and self-assembly of regioregular polythiophene by block copolymerization: Nanowire morphologies in new di- and triblock copolymers,”Angewandte Chemie International English Edition, vol. 41, No. 2, 2002.
To et al., “Solvent dependence of the evolution of the surface morphology of thin asymmetric diblock copolymer films,”Thin Solid Films, vol. 467, pp. 59-64, 2004.
Search Report, European Application No. EP 07 73 8838 dated Aug. 26, 2010.

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