TY - JOUR
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.
N1 - Funding Information:
This study was supported by a Grant-in-Aid (No. 09670913) for Scientific Research from the Ministry of Education, Science and Culture, Japan.
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.
UR - http://www.scopus.com/inward/record.url?scp=0033991881&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0033991881&partnerID=8YFLogxK
U2 - 10.1016/S0969-8043(99)00117-7
DO - 10.1016/S0969-8043(99)00117-7
M3 - Article
C2 - 10670927
AN - SCOPUS:0033991881
VL - 52
SP - 87
EP - 92
JO - Applied Radiation and Isotopes
JF - Applied Radiation and Isotopes
SN - 0969-8043
IS - 1
ER -