Synthesis of pH indicators for Cerenkov imaging by electrophilic substitution of bromine by fluorine in an aromatic system.

ABSTRACT: Direct electrophilic fluorination using molecular fluorine gas is used in organic synthesis to create novel fluorine-containing compounds with potential beneficial activity that could not be obtained by nucleophilic substitution. In this paper, we report a novel electrophilic substitution of bromine by fluorine in an aromatic system. The mechanism of this type of fluorination was explored using the reaction between bromothymolsulfonphthalein (Bromothymol Blue) and dilute fluorine gas under acidic conditions. Substitution occurs in the bromine atoms located in the ortho-position relative to the hydroxyl group. A similar electrophilic fluorination of thymolsulfonphthalein (Thymol Blue) leads to a substitution of hydrogen atoms in the same position (ortho to hydroxyl). NMR spect

SUBMITTER: Kachur AV 

PROVIDER: S-EPMC5630228 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature