Sulfuric Acid → Tert-butyl 2-(2,3-difluoro-6-nitrophenyl)-3-oxobutanoate
Reaction equation
[C:1]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].CCC([O-])(C)C.[Na+].[F:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[C:22](F)[C:21]=1[F:30].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+].[Cl-].[Na+]>C1(C)C=CC=CC=1.O>[F:30][C:21]1[C:20]([F:19])=[CH:25][CH:24]=[C:23]([N+:26]([O-:28])=[O:27])[C:22]=1[CH:2]([C:3](=[O:4])[CH3:5])[C:1]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
tert-Butyl acetoacetate (3.852 g) was added to a stirred mixture of sodium tert-pentoxide (2.804 g) in toluene (26 ml) at 40° C. The mixture was heated to 70° C. and 1,2,3-trifluoro-4-nitrobenzene (2.00 g) added. The mixture was maintained at 70° C. for 3 hours. The mixture was cooled to 25° C. and 20% w/w sulphuric acid added to adjust the mixture to pH 1. Sodium bicarbonate was added to bring the mixture to pH 5. Water (5 ml) and saturated sodium chloride (5 ml) was added. The lower aqueous layer was discarded and the organic layer washed successively with water (7 ml), water (7 ml), 2.3% w/w aqueous sodium bicarbonate solution (2.75 ml) and then water (6 ml). The organic layer was distilled under reduced pressure (50 mbar), to leave a solution of tert-butyl 2-(2,3-difluoro-6-nitrophenyl)-3-oxobutanoate in toluene.
Workup
- temperatureThe mixture was maintained at 70° C. for 3 hours
- temperatureThe mixture was cooled to 25° C.
- washthe organic layer washed successively with water (7 ml), water (7 ml), 2.3% w/w aqueous sodium bicarbonate solution (2.75 ml)
- distillationThe organic layer was distilled under reduced pressure (50 mbar)
Sources & evidence
- ORD record
- ord-6cc5073a004d425b884a6db9f8c62394
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851623B2
Reaction notes
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