Chlorosulfonic acid → 4-Fluoro-3-nitrobenzene-1-sulfonyl chloride
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[Cl:11][S:12](O)(=[O:14])=[O:13]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:12]([Cl:11])(=[O:14])=[O:13])=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]Participants
3
Conditions
- Temperature
- 100 °C
Procedure
1-Fluoro-2-nitrobenzene (50.0 g, 0.354 mol) was added to chlorosulfonic acid (91 g, 0.778 mol) at 65° C. The resulting mixture was then heated to 100° C. for 18 h. The mixture was cooled to room temperature, poured over ice and extracted with methylene chloride. The combined organic layers were then washed with NaHCO3, then brine, dried over MgSO4, filtered and concentrated in vacuo to afford 4-fluoro-3-nitrobenzenesulfonyl chloride (55.3 g, 65% yield) as a brown oil.