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Purifying Fluorinated Alcohol via flash Chromatography

esona
in Organic Chemistry

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Hi everyone,

I'm working on the fluorination of sulfonamide-linked alcohols using reagents like DAST and Fluolead.

My target product is the mono-fluorinated derivative (–CH₂F). smiles code: O=S(=O)(NCCCF)c2ccc(c1ccccc1)cc2

However, I also observe the trifluorinated byproduct (–CF₃). smiles code: O=S(=O)(NCCC(F)(F)F)c2ccc(c1ccccc1)cc2

I’ve been trying to separate the two using flash column chromatography on silica, but they are very close in polarity on TLC (Hexane/Ethyl Acetate)

Has anyone had success separating –CH₂F vs. –CF₃ derivatives? Any tips on solvent systems or additives would be really appreciated!

Thanks in advance!

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