Evaluation of aromatic radiobromination by nucleophilic substitution using diaryliodonium salt precursors

Journal of Labelled Compounds & Radiopharmaceuticals
Dong ZhouJohn A Katzenellenbogen

Abstract

Radiobromine-labeled compounds can be used for positron emission tomography (PET) imaging (ie, 76 Br) and for radiation therapy (ie, 77 Br). However, the commonly used electrophilic substitution reaction using no-carrier-added radiobromide does not always afford the desired product due to the high reactivity of the brominating intermediate. A nucleophilic substitution by bromide, such as radiobromination of iodonium precursors, provides an alternative route for the synthesis of bromo-radiopharmaceuticals. The applicability of aromatic radiobromination by nucleophilic substitution using diaryliodonium salt precursors was evaluated using iodonium model compounds and [76 Br]/[77 Br]bromide. Radiobromination was observed under all conditions tested, in up to quantitative yields. A QMA cartridge treatment method and a base-free method have been developed, and no extra base is needed for either methods. The base-free conditions are mild and afford much cleaner reactions. Up to 20% water is tolerated in the reactions without reducing the radiochemical yields. No-carrier-added and carrier-added reactions afforded similar results. 4-Bromobenzaldehyde and 4-bromobenzoate have been radiosynthesized reliably and in good yields. These resul...Continue Reading

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Citations

Oct 3, 2019·Nuclear Medicine and Biology·Paul A EllisonJonathan W Engle
Aug 5, 2021·Scientific Reports·Sean R McGuinnessGraham F Peaslee

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