Thionyl Chloride → 3-(Pentafluorosulfanyl)benzoyl chloride
Reaction equation
[CH:1]1[CH:6]=[C:5]([S:7]([F:12])([F:11])([F:10])([F:9])[F:8])[CH:4]=[C:3]([C:13]([OH:15])=O)[CH:2]=1.O=S(Cl)[Cl:18]>>[F:8][S:7]([F:12])([F:11])([F:10])([F:9])[C:5]1[CH:4]=[C:3]([CH:2]=[CH:1][CH:6]=1)[C:13]([Cl:18])=[O:15]Participants
3
Procedure
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 h. 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.
Workup
- temperaturewas warmed
- temperatureto reflux
- concentrationconcentrated under reduced pressure
- dissolutionThe residue was dissolved in toluene (5 mL)
- concentrationwas concentrated under reduced pressure
- concentrationThis dilution with toluene and concentration
- customto remove residual thionyl chloride
Sources & evidence
- ORD record
- ord-188d5ae00e6d461d88b6673fc9c6cc4e
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193713B2
Reaction notes
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