Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Reexamination Certificate
2005-08-26
2008-12-30
Sullivan, Daniel M (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
C562S489000
Reexamination Certificate
active
07470809
ABSTRACT:
The present invention relates to a novel process for the production of [2-(4-fluoro-benzyl)-phenyl]-acetic acid, a compound obtainable from phthalic anhydride. The process comprises the subsequent steps a) through e):a) reacting phthalic anhydride with fluorobenzene or a derivative thereof in appropriate reaction conditions;b) over reducing the product obtained in step a) at the ketone moiety;c) reducing the product obtained in step b) with sodium dihydro-bis(2-methoxyethoxy)aluminate (Red-Al) to the corresponding alcohol;d) chlorinating the alcohol obtained in step c);e) inserting CO into the product obtained in step d) through an appropriate Pd-containing catalytic system.In an alternative embodiment, the step e) is replaced by the steps f1) and f2):f1) reacting the product obtained in step d) with sodium cyanide;f2) hydrolysing the product obtained in step f1).The present invention provides a process for the production of [2-(4-fluoro-benzyl)-phenyl]-acetic acid which is suitable for industrial scale reactors (e.g. which is cleaner and more efficient). Also, [2-(4-fluoro-benzyl)-phenyl]-acetic acid is obtained as a crystalline material with a purity >95%.
REFERENCES:
patent: 6998494 (2006-02-01), Lang et al.
patent: 7205335 (2007-04-01), Hua et al.
patent: 2002/0062041 (2002-05-01), Geissler
patent: 2002/0062401 (2002-05-01), Auslander et al.
patent: 1690042 (2005-02-01), None
patent: WO 03/048146 (2003-06-01), None
patent: WO 03/048147 (2003-06-01), None
Hahn Tetrahedron 46(1924) 1645-53.
International Search Report (PCT/EP2005/054202) PRD2295f dated Jan. 16, 2006.
De Smaele Dirk
Guillaume Michel Joseph Maurice André
Lang Yolande Lydia
Leurs Stefan Marcel Herman
Roessler Armin
Janssen Pharmaceutica N.V.
Lao Louisa
Sullivan Daniel M
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