(F-18) halofluorination: A rapid and efficient method for the incorporation of radiofluorine into organic molecules

Conference · Wed May 01 04:00:00 EDT 1985 · J. Nucl. Med.; (United States)

OSTI ID:7032498

Chi, D Y; Katzenellenbogen, J A; Kilbourn, M R; Welch, M J

The addition of halogen fluoride to olefins (Hal-F, halofluorination, where Hal is Br or I) is a more favorable reaction for labeling with tracer levels of F-18 than is addition of hydrogen fluoride (H-F, hydrofluorination), because of the more productive soft acid-soft base interaction between the Hal and the olefin. The authors have found that simple olefins (allylbenzene, 1-hexene, 1-propene) undergo rapid bromofluorination when treated with 1,3-dibromo-5,5-dimethylhydantoin (DBH), giving a 7:1 mixture of Markownikow (M) and anti-Markownikow (AM) adducts. In chlorinated solvents, the reaction is rapid and efficient, giving yields of 50-90% based on fluoride as limiting reagent. The products can be reduced to the fluorocarbon by debromination (R/sub 3/SnH or LiAlH/sub 4/), or they can be used to alkylate amines. Reasonable radiochemical yields can be obtained using F-18 produced in a water target (/sup 18/O(p,n)/sup 18/F), in either carrier-added (20-50%) or no-carrier-added (ca. 10-20%) modes. This reaction is being used to prepare F-18 labeled radiopharmaceuticals.

• Research Organization: Univ. of Illinois, Urbana, IL
• OSTI ID: 7032498
• Report Number(s): CONF-850611-
• Conference Information: Journal Name: J. Nucl. Med.; (United States) Journal Volume: 26:5
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201 -- Chemical & Physicochemical Properties
550601* -- Medicine-- Unsealed Radionuclides in Diagnostics
62 RADIOLOGY AND NUCLEAR MEDICINE
BETA DECAY RADIOISOTOPES
BETA-PLUS DECAY RADIOISOTOPES
BIOCHEMICAL REACTION KINETICS
CHEMICAL PREPARATION
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHEMISTRY
DRUGS
EFFICIENCY
FLUORINATION
FLUORINE 18
FLUORINE ISOTOPES
HALOGENATION
HOURS LIVING RADIOISOTOPES
ISOTOPES
KINETICS
LABELLED COMPOUNDS
LABELLING
LIGHT NUCLEI
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC FLUORINE COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
RADIOCHEMISTRY
RADIOISOTOPES
RADIOPHARMACEUTICALS
REACTION KINETICS
SYNTHESIS
YIELDS