Oxidation of substituted 4-fluorobenzaldehydes: Application to the no-carrier-added syntheses of 4-[18F]fluoroguaiacol and 4-[18F]fluorocatechol |
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| Affiliation: | 1. Orthopaedic Surgery, Stanford Hospital, Stanford, California;2. Palo Alto VA Hospital, Palo Alto, California;1. State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Jilin University, Changchun 130012, PR China;2. Institute of Carbon Materials Science, Shanxi Datong University, Datong 037009, PR China;3. Key Laboratory of Physics and Technology for Advanced Batteries, Ministry of Education, College of Physics, Jilin University, Changchun 130012, PR China;1. Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 København Ø, Denmark;2. Center for Integrated Molecular Brain Imaging (CIMBI), Rigshospitalet and University of Copenhagen, Blegdamsvej 9, 2100 Copenhagen, Denmark;3. Department of Clinical Physiology, Nuclear Medicine and PET, Rigshospitalet, Blegdamsvej 9, 2100 Copenhagen, Denmark;1. Institute of Physical Chemistry, Saarland University, Campus B 2.2, 66123 Saarbrücken, Germany;2. Korea Institute of Science and Technology Europe, Campus E 7.1, 66123 Saarbrücken, Germany;1. University of Castilla-La Mancha, Institute for Nanoscience, Nanotechnology and Molecular Materials (INAMOL), Campus de la Fábrica, 45071 Toledo, Spain;2. Institute of Organic Chemistry II and Advanced Materials, Ulm University, Albert-Einstein-Alle 11, 89081 Ulm, Germany;1. Università degli Studi di Firenze, NEUROFARBA Dept., Sezione di Scienze Farmaceutiche, Via Ugo Schiff 6, 50019 Sesto Fiorentino (Florence), Italy;2. Università degli Studi di Firenze, Polo Scientifico, Laboratorio di Chimica Bioinorganica, Rm. 188, Via della Lastruccia 3, 50019 Sesto Fiorentino (Florence), Italy |
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| Abstract: | The synthesis of 4-[18F]fluoroguaiacol (4-[18F]fluoro-2-methoxyphenol) has been achieved in no-carrier-added form starting from 2-methoxy-4-nitrobenzaldehyde, using nucleophilic aromatic substitution by [18F]fluoride followed by Baeyer-Villiger oxidation of the benzaldehyde to the phenol. Demethylation with boron tribromide gave 4-[18F]fluorocatechol (1,2-dihydroxy-4-[18F]fluorobenzene) with an overall yield of 18–28% (EOB) in less than 2 h synthesis time. The fluorine-18 labeled intermediates and products were identical to standards of 4-fluoroguaiacol and 4-fluorocatechol prepared by the same methods. This represents a new approach to the synthesis of fluorinated phenols in fluorine-19 and fluorine-18 forms. |
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