A new, convenient method for the preparation of 4-[18F]fluorobenzyl halides

R. Iwata; C. Pascali; A. Bogni; G. Horvath; Z. Kovács; K. Yanai; T. Ido

doi:10.1016/S0969-8043(99)00117-7

A new, convenient method for the preparation of 4-[¹⁸F]fluorobenzyl halides

R. Iwata, C. Pascali, A. Bogni, G. Horvath, Z. Kovács, K. Yanai, T. Ido

MED - Medical Sciences

Research output: Contribution to journal › Article › peer-review

39 Citations (Scopus)

Abstract

A convenient method suitable for automated preparation of 4- [¹⁸F]fluorobenzyl halides from no-carrier-added [¹⁸F]fluoride has been developed. 4-[¹⁸F]Fluorobenzaldehyde, synthesized from [¹⁸F]fluoride by aromatic nucleophilic substitution on 4-trimethylammoniumbenzaldehyde triflate, was first retained on a C18 cartridge and there efficiently reduced to 4-[¹⁸F]fluorobenzyl alcohol simply by flowing an aqueous solution of NaBH₄. The conversion of 4-[¹⁸F]fluorobenzyl alcohol to 4- [¹⁸F]fluorobenzyl halide was investigated using PBr₃, PI₃, P₂I₄, Ph₃PBr₂ and Ph₃PI₂ in CH₂Cl₂. 4-[¹⁸F]Fluorobenzyl halides were purified by passing through a disposable silica cartridge. The conversion rapidly proceeded in radiochemical yields of nearly 90% at 40°C with P₂I₄ and almost quantitatively at room temperature with Ph₃PBr₂. With this last reagent 4-[¹⁸F]fluorobenzyl bromide was obtained in overall radiochemical yields of 50-60% within 30 min from EOB.

Original language	English
Pages (from-to)	87-92
Number of pages	6
Journal	Applied Radiation and Isotopes
Volume	52
Issue number	1
DOIs	https://doi.org/10.1016/S0969-8043(99)00117-7
Publication status	Published - 2000 Jan

ASJC Scopus subject areas

Radiation

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title = "A new, convenient method for the preparation of 4-[18F]fluorobenzyl halides",

abstract = "A convenient method suitable for automated preparation of 4- [18F]fluorobenzyl halides from no-carrier-added [18F]fluoride has been developed. 4-[18F]Fluorobenzaldehyde, synthesized from [18F]fluoride by aromatic nucleophilic substitution on 4-trimethylammoniumbenzaldehyde triflate, was first retained on a C18 cartridge and there efficiently reduced to 4-[18F]fluorobenzyl alcohol simply by flowing an aqueous solution of NaBH4. The conversion of 4-[18F]fluorobenzyl alcohol to 4- [18F]fluorobenzyl halide was investigated using PBr3, PI3, P2I4, Ph3PBr2 and Ph3PI2 in CH2Cl2. 4-[18F]Fluorobenzyl halides were purified by passing through a disposable silica cartridge. The conversion rapidly proceeded in radiochemical yields of nearly 90% at 40°C with P2I4 and almost quantitatively at room temperature with Ph3PBr2. With this last reagent 4-[18F]fluorobenzyl bromide was obtained in overall radiochemical yields of 50-60% within 30 min from EOB.",

author = "R. Iwata and C. Pascali and A. Bogni and G. Horvath and Z. Kov{\'a}cs and K. Yanai and T. Ido",

year = "2000",

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T1 - A new, convenient method for the preparation of 4-[18F]fluorobenzyl halides

AU - Iwata, R.

AU - Pascali, C.

AU - Bogni, A.

AU - Horvath, G.

AU - Kovács, Z.

AU - Yanai, K.

AU - Ido, T.

PY - 2000/1

Y1 - 2000/1

N2 - A convenient method suitable for automated preparation of 4- [18F]fluorobenzyl halides from no-carrier-added [18F]fluoride has been developed. 4-[18F]Fluorobenzaldehyde, synthesized from [18F]fluoride by aromatic nucleophilic substitution on 4-trimethylammoniumbenzaldehyde triflate, was first retained on a C18 cartridge and there efficiently reduced to 4-[18F]fluorobenzyl alcohol simply by flowing an aqueous solution of NaBH4. The conversion of 4-[18F]fluorobenzyl alcohol to 4- [18F]fluorobenzyl halide was investigated using PBr3, PI3, P2I4, Ph3PBr2 and Ph3PI2 in CH2Cl2. 4-[18F]Fluorobenzyl halides were purified by passing through a disposable silica cartridge. The conversion rapidly proceeded in radiochemical yields of nearly 90% at 40°C with P2I4 and almost quantitatively at room temperature with Ph3PBr2. With this last reagent 4-[18F]fluorobenzyl bromide was obtained in overall radiochemical yields of 50-60% within 30 min from EOB.

AB - A convenient method suitable for automated preparation of 4- [18F]fluorobenzyl halides from no-carrier-added [18F]fluoride has been developed. 4-[18F]Fluorobenzaldehyde, synthesized from [18F]fluoride by aromatic nucleophilic substitution on 4-trimethylammoniumbenzaldehyde triflate, was first retained on a C18 cartridge and there efficiently reduced to 4-[18F]fluorobenzyl alcohol simply by flowing an aqueous solution of NaBH4. The conversion of 4-[18F]fluorobenzyl alcohol to 4- [18F]fluorobenzyl halide was investigated using PBr3, PI3, P2I4, Ph3PBr2 and Ph3PI2 in CH2Cl2. 4-[18F]Fluorobenzyl halides were purified by passing through a disposable silica cartridge. The conversion rapidly proceeded in radiochemical yields of nearly 90% at 40°C with P2I4 and almost quantitatively at room temperature with Ph3PBr2. With this last reagent 4-[18F]fluorobenzyl bromide was obtained in overall radiochemical yields of 50-60% within 30 min from EOB.

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