Phosphorus pentachloride → (4-Fluoro-3-phenoxyphenyl)methanesulfonyl chloride
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([O-])(=[O:11])=[O:10])=[CH:4][C:3]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Na+].P(Cl)(Cl)(Cl)(Cl)[Cl:22]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([Cl:22])(=[O:11])=[O:10])=[CH:4][C:3]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1Participants
3
Procedure
The sodium sulfonate obtained in step 1 is mixed with phosphorous pentachloride at room temperature for two days. An ice-water mixture is added and the aqueous solution is extracted with methylene chloride. The organic extract is washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain (4-fluoro-3-phenoxyphenyl)methanesulfonyl chloride as a syrup (2.05 g).
Workup
- extractionthe aqueous solution is extracted with methylene chloride
- extractionThe organic extract
- washis washed with water