Title:
PROCESS FOR THE PREPARATION OF FLUOROHALOALKANES
Document Type and Number:
WIPO Patent Application WO2004029006
Kind Code:
A3
Abstract:
The invention provides a process for preparation of a fluorohaloalkane, preferably an [<18>F]fluorohaloalkane of formula (I) wherein X is halo and n is an integer of from 1 to 6; which comprises: reaction of the corresponding organosilicon compound of formula (II): wherein n is as defined for the compound of formula (I); and R', R", and R"' are independently selected from C1-6 alkyl and C1-6 haloalkyl; and R'' may alternatively be the group, with a compound of formula (III), wherein X is as defined for the compound of formula (I) and Y is halo. Intermediates having use in such processes are also claimed.
Inventors:
BRADY FRANK (GB)
LUTHRA SAJINDER (GB)
ZHAO YONGJUN (GB)
LUTHRA SAJINDER (GB)
ZHAO YONGJUN (GB)
Application Number:
PCT/GB2003/004026
Publication Date:
May 13, 2004
Filing Date:
September 18, 2003
Export Citation:
Assignee:
HAMMERSMITH IMANET LTD (GB)
BRADY FRANK (GB)
LUTHRA SAJINDER (GB)
ZHAO YONGJUN (GB)
BRADY FRANK (GB)
LUTHRA SAJINDER (GB)
ZHAO YONGJUN (GB)
International Classes:
C07B59/00; C07C17/093; C07C303/26; (IPC1-7): C07B59/00; C07C17/093; C07B39/00; C07F7/08
Foreign References:
| JPH02290885A | 1990-11-30 |
Other References:
ZHANG M-R ET AL: "Development of an automated system for synthesizing F-labeled compounds using [F]fluoroethyl bromide as a synthetic precursor", APPLIED RADIATION AND ISOTOPES, PERGAMON PRESS LTD., EXETER, GB, vol. 57, no. 3, September 2002 (2002-09-01), pages 335 - 342, XP004370242, ISSN: 0969-8043
E.S. ALEXANDER ET AL.: "Polyfluoroalkyl Compounds of SIlicon. Part IX. Silanes containing the Bis(trifluoromethyl)amino-group", J. CHEM. SOC. A, 1970, pages 2285 - 91, XP002266201
DIETMAR SEYFERTH ET AL.: "Halomethyl-metal compounds. Phenyl(fluorodibromomethyl)mercury, a fluorobromocarbene precursor", J. ORGANOMET. CHEM., vol. 51, 1973, pages 77 - 87, XP002266202
EDMUND K.S. LIU ET AL: "Fluorination of dimethylmercury, tetramethylsilane and tetramethylgermanium", J. ORGANOMET. CHEM., 1978, pages 167 - 82, XP002266203
ROGER L. SCHOLL ET AL.: "Silicon-29 Chemical Shifts of Organosilicon Compounds", J. AM. CHEM. SOC., vol. 94, no. 18, 1972, pages 6376 - 85, XP002266204
D. COOPER ET AL.: "Polyfluoroalkyl Compounds of Silicon. VIII Reactions of Silanes with Vinyl Fluoride and with 1-Chloro-2-fluoroethylene", J. CHEM. SOC. A, vol. 196, 1967, pages 2098 - 2103, XP002266205
J. VCELAK ET AL.: "The exchange of fluorine in (gamma-fluoropropyl)trialkylsilanes and n-heptyl fluoride for halogens of grignard reagents", COLLECTION CZECHOSLOV. CHEM. COMMUN., vol. 41, 1976, pages 131 - 9, XP008028871
J. VCELAK ET AL.: "19F-NMR spectra of (Fluoroalkyl)-Substituted Silanes", COLLECTION CZECHOSLOV. CHEM. COMMUN., vol. 41, 1976, pages 386 - 390, XP008028870
V.B. PUCHNAREVIC ET AL.: "Synthesis of gamma-fluoropropyl Substituted Silanes", COLLECTION CZECHOSLOV. CHEM. COMMUN., vol. 39, 1974, pages 2616 - 2620, XP008028872
E.S. ALEXANDER ET AL.: "Polyfluoroalkyl Compounds of SIlicon. Part IX. Silanes containing the Bis(trifluoromethyl)amino-group", J. CHEM. SOC. A, 1970, pages 2285 - 91, XP002266201
DIETMAR SEYFERTH ET AL.: "Halomethyl-metal compounds. Phenyl(fluorodibromomethyl)mercury, a fluorobromocarbene precursor", J. ORGANOMET. CHEM., vol. 51, 1973, pages 77 - 87, XP002266202
EDMUND K.S. LIU ET AL: "Fluorination of dimethylmercury, tetramethylsilane and tetramethylgermanium", J. ORGANOMET. CHEM., 1978, pages 167 - 82, XP002266203
ROGER L. SCHOLL ET AL.: "Silicon-29 Chemical Shifts of Organosilicon Compounds", J. AM. CHEM. SOC., vol. 94, no. 18, 1972, pages 6376 - 85, XP002266204
D. COOPER ET AL.: "Polyfluoroalkyl Compounds of Silicon. VIII Reactions of Silanes with Vinyl Fluoride and with 1-Chloro-2-fluoroethylene", J. CHEM. SOC. A, vol. 196, 1967, pages 2098 - 2103, XP002266205
J. VCELAK ET AL.: "The exchange of fluorine in (gamma-fluoropropyl)trialkylsilanes and n-heptyl fluoride for halogens of grignard reagents", COLLECTION CZECHOSLOV. CHEM. COMMUN., vol. 41, 1976, pages 131 - 9, XP008028871
J. VCELAK ET AL.: "19F-NMR spectra of (Fluoroalkyl)-Substituted Silanes", COLLECTION CZECHOSLOV. CHEM. COMMUN., vol. 41, 1976, pages 386 - 390, XP008028870
V.B. PUCHNAREVIC ET AL.: "Synthesis of gamma-fluoropropyl Substituted Silanes", COLLECTION CZECHOSLOV. CHEM. COMMUN., vol. 39, 1974, pages 2616 - 2620, XP008028872
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