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Direct iodination of estradiol 17β-acetate (3) using iodine–copper(II) acetate in acetic acid afforded the 2-iodo derivative regioselectively in high yield. The iodination of 3 using several methods was discussed. On the other hand, the reaction of 3 with iodine–copper(II) bromide gave the 4-bromo derivative (7), not the 2-iodo compound. The reaction of 3-methoxy-17β-acetoxy-1,3,5(10)-estratriene (4) with iodine–copper(II) chloride–iron(III) chloride in acetic acid gave the 2- (10) and 4-iodo (11) derivative.
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Horiuchi et al. (1986) studied this question.
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