Regioselective A-ring iodination of estradiol diacetates

Treatment of estrone or estradiol acetate with thallium trifluoroacetate in TFA and subsequent reaction with KI gave the 2-iodoestrogens as the major product. In the case of estradiol diacetate, treatment of the thallation product with [125I]NaI, using the same reaction conditions, gave exclusively the 2-iodo isomer. Thus, regioselectivity combined with rapidity, renders this procedure particularly suitable for A-ring radioiodination of estradiol with short-lived isotopes.