Microwave-induced nucleophilic [18F]fluorination on aromatic rings:: Synthesis and effect of halogen on [18F]fluoride substitution of meta-halo (F, Cl, Br, I)-benzonitrile derivatives

被引：14

作者：

Guo, Ning ^{[1
]}

Alagille, David ^{[2
]}

Tamagnan, Gilles ^{[2
]}

Price, Ronald R. ^{[1
]}

Baldwin, Ronald M. ^{[1
]}

机构：

[1] Vanderbilt Univ, Sch Med, Dept Radiol & Radiol Sci, Nashville, TN 37232 USA

[2] Mol Neuroimaging Inc, New Haven, CT 06510 USA

来源：

APPLIED RADIATION AND ISOTOPES | 2008年 / 66卷 / 10期

基金：

美国国家卫生研究院;

关键词：

fluorine-18; radiolabeling; microwave; PET tracer; organic synthesis; substituent effect;

D O I：

10.1016/j.apradiso.2008.03.003

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The meta-halo-3-methylbenzonitrile derivatives (-F, -Cl, -Br, -I) were synthesized as model compounds to study reactivity towards aromatic nucleophilic Substitution. A single-mode microwave system was incorporated into a commercial radiochemical synthetic module for F-18 labeling. Labeling yields of 64% for fluoro-, 13% for bromo- and 9% for chloro-precursors were achieved in DMSO in < 3 min. The observed order of reactivity of the leaving groups toward aromatic nucleophilic substitution was F >> Br > Cl >>> I. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：1396 / 1402

页数：7

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