Fluorination of aromatic compounds by cleavage of aryl-tin bonds with F-18 F/sub 2/ and CH/sub 3/COOF

Conference · Sun Jan 01 04:00:00 EST 1984 · J. Nucl. Med.; (United States)

OSTI ID:6843010

Adam, M J; Abeysekera, B F; Ruth, T J; Jivan, S; Pate, B D

Direct fluorination of aromatic nuclei is difficult since the reaction is usually accompanied by unselective, partial, or total replacement of hydrogen. By attaching the tri-n-butyltin moiety to one position of the ring one can achieve an enhanced reactivity and site selectivity toward electrophilic fluorination. The intent of this study was to demonstrate the utility of the fluorodestannylation reaction for fluorine labelling of aromatic compounds and to compare F/sub 2/ and acetyl hypofluorite as the fluorinating agents. Thus, eight stannylated aromatic compounds (1-8) were synthesized via lithium halogen exchange of the bromo precursor and subsequent transmetallation using tri-n-butyltin chloride. The stannylated substrates were treated with F-18 F/sub 2/ and -78/sup 0/C and CH/sub 3/COOF at room temperature. Both reagents gave good yields of labelled aryl fluorides. Overall, acetyl hypofluorite gave more consistent yields (approx. =70%), while F/sub 2/ gave more variable yields (54-95%). This method is currently being extended to label more complex systems such as L-Dopa with F-18 for brain studies with positron emission tomography. The authors have successfully stannylated Dopa on the ring and fluorination studies of this substrate are underway.

• Research Organization: TRIUMF, Vancouver, BC
• OSTI ID: 6843010
• Report Number(s): CONF-840619-
• Conference Information: Journal Name: J. Nucl. Med.; (United States) Journal Volume: 25:5
• Country of Publication: United States
• Language: English

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62 RADIOLOGY AND NUCLEAR MEDICINE
ACTIVATION ENERGY
ALKALINE EARTH METAL COMPOUNDS
AMINO ACIDS
AROMATICS
ARYL RADICALS
AUTONOMIC NERVOUS SYSTEM AGENTS
BETA DECAY RADIOISOTOPES
BETA-PLUS DECAY RADIOISOTOPES
BODY
BRAIN
CALCIUM COMPOUNDS
CALCIUM FLUORIDES
CALCIUM HALIDES
CARBOXYLIC ACIDS
CENTRAL NERVOUS SYSTEM
CHEMICAL PREPARATION
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHLORIDES
CHLORINE COMPOUNDS
COMPUTERIZED TOMOGRAPHY
DIAGNOSTIC TECHNIQUES
DIAGNOSTIC USES
DOPA
DRUGS
ELEMENTS
EMISSION COMPUTED TOMOGRAPHY
ENERGY
FLUORIDES
FLUORINATION
FLUORINE 18
FLUORINE COMPOUNDS
FLUORINE ISOTOPES
FLUORITE
HALIDE MINERALS
HALIDES
HALOGEN COMPOUNDS
HALOGENATION
HOURS LIVING RADIOISOTOPES
HYDROGEN
HYDROXY ACIDS
ISOTOPES
LABELLING
LIGHT NUCLEI
LOW TEMPERATURE
MINERALS
NERVOUS SYSTEM
NEUROREGULATORS
NONMETALS
NUCLEI
ODD-ODD NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANS
POSITRON COMPUTED TOMOGRAPHY
RADICALS
RADIOISOTOPES
SUBSTRATES
SYNTHESIS
TIN COMPOUNDS
TOMOGRAPHY
USES
YIELDS