Thionyl Chloride → 3-(Pentafluorosulfanyl)benzoyl chloride

Participants

Reaction Steps

A mixture of 3-(pentafluorothio)benzoic acid (Apollo Scientific, 0.42 g, 1.7 mmol) and SOCl2 (1.2 mL, 16.9 mmol) was warmed to reflux and was allowed to stir for 2 hours. The mixture was cooled to ambient temperature and concentrated under reduced pressure. The residue was dissolved in toluene (5 mL) and was concentrated under reduced pressure. This dilution with toluene and concentration was repeated two additional times to remove residual thionyl chloride and afford 3-(pentafluoro-λ6-sulfanyl)benzoyl chloride that was used directly below.

Provenance & Evidence