4-[18F]fluoroarylalkylethers via an improved synthesis of n.c.a. 4-[18F]fluorophenol.
This paper describes the improved synthesis of n.c.a. 4- 18F]fluorophenol for the preparation of 18F-labeled alkylarylethers. Nucleophilic fluorination of substituted benzophenone derivatives yielded n.c.a. 4- 18F]fluoro-4'-substituted benzophenones with 80- 90% RCY, which were converted to benzoic acid phenylesters by treatment with peracetic acid. Strong electron-withdrawing substituents like nitro, cyano and trifluoromethyl favor a fluorophenyl-to-oxygen migration resulting in the formation of corresponding benzoic acid fluorophenylesters. N.c.a. 18F]fluorophenol is almost quantitatively formed after hydrolysis and can easily be converted with alkylhalides into n.c.a. 18F]fluoroarylalkylethers.
Ludwig
Thomas
T
Institut für Nuklearchemie, Forschungszentrum Jülich GmbH, D-52425, Jülich, Germany.
Ermert
Johannes
J
Coenen
Heinz H
HH
D000473:Alkanes / Q000138:chemical synthesis / Q000737:chemistry; D004987:Ethers / Q000138:chemical synthesis / Q000737:chemistry; D005462:Fluorine Radioisotopes / Q000737:chemistry; D010636:Phenols / Q000138:chemical synthesis*
D000473:Alkanes; D004987:Ethers; D005462:Fluorine Radioisotopes; D010636:Phenols; C106880:4-fluorophenol