Dimethyl Sulfoxide → 4-Chloro-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran-3-one
Reaction equation
Br[CH:2]1[C:6]2[C:7]([Cl:14])=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:5]=2[O:4][C:3]1([CH3:16])[CH3:15].C(N(CC)CC)C.CS(C)=[O:26]>F[B-](F)(F)F.[Ag+]>[Cl:14][C:7]1[C:6]2[C:2](=[O:26])[C:3]([CH3:16])([CH3:15])[O:4][C:5]=2[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=1Participants
Conditions
- Temperature
- 60 °C
Procedure
A solution of 15.0 g (0.0489 mole) of 3-bromo-4-chloro-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran in 100 mL of dimethyl sulfoxide was added slowly to a mixture of 9.73 g (0.050 mole) of silver tetrafluoroborate in 100 mL of dimethyl sulfoxide. Upon completion of addition, 5.0 g (0.050 mole) of triethylamine was added to the reaction mixture, and stirring was continued for approximately 16 hours at ambient temperature. At the conclusion of this period the reaction mixture was heated at 60° C. for one hour and then cooled to ambient temperature. The mixture was filtered, and the filtrate was poured into 200 mL of water. This mixture was extracted with diethyl ether. The extract was dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated from the filtrate under reduced pressure, leaving a residue. This residue was passed through a column of silica gel, yielding 5.35 g of 4-chloro-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran-3-one as a solid residue, m.p. 167°-168° C.
Workup
- additionwas added to the reaction mixture
- temperaturecooled to ambient temperature
- filtrationThe mixture was filtered
- additionthe filtrate was poured into 200 mL of water
- extractionThis mixture was extracted with diethyl ether
- dry with materialThe extract was dried over anhydrous magnesium sulfate
- filtrationfiltered
- customthe solvent was evaporated from the filtrate under reduced pressure
- customleaving a residue
Sources & evidence
- ORD record
- ord-f911b54315eb4438875afbb8c0854477
- Source dataset
- uspto-grants-1996_05
- Patent number
- US05521147
Reaction notes
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