Syntheses of Regioisomerically Pure 5- or 6-Halogenated Fluoresceins

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Abstract
Three routes to regioisomerically pure 5- and 6-iodofluoresceins or 5- and 6-bromofluoresceins are described. The first, shown in Scheme 1, involves diazotization/iodination of the corresponding aminofluoresceins. In the second approach (Scheme 2) a mixture of regioisomeric fluoresceins was prepared, and the 5-bromo isomers were isolated as the ring closed diacetates 9b and 11 by fractional crystallization. Scheme 3 shows an approach to sulfonic acid derivatives 3 and 4 of 5-iodofluorescein. This is the most convenient procedure of the three, and it is particularly useful as sulfofluoresceins have more favorable water solubility characteristics than fluoresceins that lack the sulfonic acid group.

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