Phosphorus oxychloride → 8-Oxatricyclo(7.4.0.0,2,7)trideca-1(9),2(7),3,5,10,12-hexaene-4-sulfonyl chloride
Reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[S:14]([OH:17])(=O)=[O:15].P(Cl)(Cl)([Cl:20])=O>>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[S:14]([Cl:20])(=[O:17])=[O:15]Participants
3
Procedure
2-Dibenzofuransulfonic acid (12.8 mmol) was heated at 70° C. with phosphorus oxychloride (1.30 ml, 14.0 mol) for 2 h. Excess phosphorus oxychloride was removed under reduced pressure. The residue was decomposed with ice water and extracted with ethyl acetate. The extract was washed with 5% sodium bicarbonate solution, dried over anhydrous magnesium sulfate and concentrated to yield 2.9 g crude 2-dibenzofuransulfonyl chloride.
Workup
- customExcess phosphorus oxychloride was removed under reduced pressure
- extractionextracted with ethyl acetate
- washThe extract was washed with 5% sodium bicarbonate solution
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c1bd756b4f7b4e9ba79d88a12055f4c5
- Source dataset
- uspto-grants-2002_01
- Patent number
- US06342610B2
Reaction notes
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