2-Bromopropane → 4-Fluoro-2-isopropoxy-1-nitrobenzene
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:19]([CH3:21])[CH3:20]>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([O:8][CH:19]([CH3:21])[CH3:20])[CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 22 °C
Procedure
A suspended orange mixture of 5-fluoro-2-nitrophenol (XVIII, 10.0 g, 63.6 mmol), potassium carbonate (8.84 g, 64.0 mmol) and 2-bromopropane (6.00 mL, 63.6 mmol) in dimethyiformamide (63.0 mL) was stirred at 22° C. under argon. After 1 d, an additional 2.0 mL of 2-bromopropane was added and the resultant mixture was heated at 60° C. for 1 do The reaction mixture was then partitioned between methylene chloride and 3N NaOH. The organic layer was separated and the basic aqueous layer was extracted with additional methylene chloride. The combined organic solution was washed with water (5×200 mL), dried (MgSO4), filtered and concentrated to provide 12.02 g (95%) of an orange oil, 95% pure by GC, which was carried on without further purification. The structure was supported by MS and 90 MHz 1H NMR.
Workup
- customwas then partitioned between methylene chloride and 3N NaOH
- customThe organic layer was separated
- extractionthe basic aqueous layer was extracted with additional methylene chloride
- washThe combined organic solution was washed with water (5×200 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-509d89a2b2d14235974d15c6b9dc8bae
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05569659
Reaction notes
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