Radiolabeling of aromatic compounds using K[ * Cl]Cl and OXONE ®

We report a novel labeling method for the rapid radiochlorination of aromatic compounds using no‐carrier‐added short‐half‐life radioactive chloride ions ([ 38,39 Cl]Cl − and [ 34m Cl]Cl − ) and OXONE® (Sigma‐Aldrich, Japan) as an oxidation reagent. The reaction of radioactive chloride ions with anisole in the presence of OXONE gave a mixture of p ‐[ * Cl]chloroanisole and o ‐[ * Cl]‐chloroanisole, with a radiochemical conversion yield of more than 85% (not decay corrected) and selectivity of 7:3, within 10 min. Regioselective radioactive chlorination was achieved by chlorodestannylation of tributylstannyl compounds to afford the corresponding radiochlorinated compounds ( p ‐chloroanisole and m ‐chloroanisole) in satisfactory radiochemical yields (80–95% and 46–65%, respectively). Copyright © 2012 John Wiley & Sons, Ltd.