Isopropanol → 1-Bromo-5-isopropoxy-2-methyl-4-nitrobenzene
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6](F)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH3:12].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:19][CH:20]([OH:22])[CH3:21]>>[Br:1][C:2]1[CH:7]=[C:6]([O:22][CH:20]([CH3:21])[CH3:19])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH3:12]Participants
4
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 1-bromo-5-fluoro-2-methyl-4-nitrobenzene (Step 1, 1.5 g, 6.4 mmol) in 2-propanol (30 mL) was added cesium carbonate (5.3 g, 16 mmol). The mixture was heated at 50° C. overnight. The mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was concentrated and the residue was purified with silica gel column chromatography with 5% ethyl acetate in hexanes to afford 1-bromo-5-isopropoxy-2-methyl-4-nitrobenzene as a yellow solid.
Workup
- concentrationThe mixture was concentrated
- custompartitioned between ethyl acetate and water
- concentrationThe organic layer was concentrated
- customthe residue was purified with silica gel column chromatography with 5% ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-a209a1cc9d4e4e8f81abc95314bfd2ab
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08859574B2
Reaction notes
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