Syntheses of (/sup 18/F) aryl fluorides by fluorination of aryltrimethylsilanes or arylpentafluorosilicates with (/sup 18/F)F/sub 2/ or (/sup 18/F)CH/sub 3/CO/sub 2/F

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

OSTI ID:6758651

Speranza, M; Shiue, C Y; Wolf, A P; Wilbur, D S

F-18 Aryl fluorides are the important intermediates for the syntheses of F-18 labeled radiopharmaceuticals. F-18 Labeled aryl fluorides have been synthesized either from (/sup 18/F)F/sub 2/ or (/sup 18/F)fluoride. The authors report here the syntheses of (/sup 18/F)aryl fluorides by fluorination of aryltrimethylsilanes (1) or arylpentaflurorsilicates (2) with (/sup 18/F)F/sub 2/ or (/sup 18/F)CH/sub 3/CO/sub 2/F. Fluorination of compounds (1) with either (/sup 18/F)F/sub 2/ or (/sup 18/F)CH/sub 3/CO/sub 2/F give the corresponding aryl fluorides (3) and the aryltrimethylsilyl fluorides (4) in 2-10% yields depending on the reaction conditions. Compounds (2) and (3) can easily be separate by HPLC or GLC. Treatment of compounds (4) with HClO/sub 4/-MeOH (1:1) give the corresponding desilylated compounds (3underscore). Fluorination of compounds (2) with (/sup 18/F)CH/sub 3/CO/sub 2/F give the corresponding aryl fluorides (3) in 10-20% yield. The yields of compounds (3) and (4) depend on the reaction conditions. Lower temperature (-76/sup 0/C in freon vs 25/sup 0/C in CH/sub 3/CO/sub 2/H) favors the formation of aryl fluorides, (/sup 18/F)F/sub 2/ gives a better yield of aryl fluorides than with (/sup 18/F)CH/sub 3/CO/sub 2/F, and the electron-withdrawing groups are in favor of aryl fluoride formations. This method thus provides an alternative route to F-18 labeled radiopharmaceuticals such as p-/sup 18/F)fluorohippuric acid which is otherwise difficult to prepare, and other F-18 labeled neuroleptics.

• Research Organization: Brookhaven National Lab., Upton, NY
• OSTI ID: 6758651
• Report Number(s): CONF-840619-; TRN: 87-010908
• Journal Information: J. Nucl. Med.; (United States), Vol. 25:5; Conference: 31. annual meeting of the Society of Nuclear Medicine, Los Angeles, CA, USA, 5 Jun 1984
• Country of Publication: United States
• Language: English

Related Subjects

62 RADIOLOGY AND NUCLEAR MEDICINE
38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
FLUORINATED AROMATIC HYDROCARBONS
CHEMICAL PREPARATION
LABELLING
FLUORINE 18
RADIOCHEMISTRY
SILANES
FLUORINATION
GAS CHROMATOGRAPHY
LIQUID COLUMN CHROMATOGRAPHY
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
RADIOPHARMACEUTICALS
REACTION INTERMEDIATES
AROMATICS
BETA DECAY RADIOISOTOPES
BETA-PLUS DECAY RADIOISOTOPES
CHEMICAL REACTIONS
CHEMISTRY
CHROMATOGRAPHY
DRUGS
FLUORINE ISOTOPES
HALOGENATED AROMATIC HYDROCARBONS
HALOGENATION
HOURS LIVING RADIOISOTOPES
HYDRIDES
HYDROGEN COMPOUNDS
ISOTOPES
KINETICS
LABELLED COMPOUNDS
LIGHT NUCLEI
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC FLUORINE COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC SILICON COMPOUNDS
RADIOISOTOPES
REACTION KINETICS
SEPARATION PROCESSES
SILICON COMPOUNDS
SYNTHESIS
YIELDS
550601* - Medicine- Unsealed Radionuclides in Diagnostics
400700 - Radiochemistry & Nuclear Chemistry