Water → 2-Bromo-1-methoxy-4-(trifluoromethoxy)benzene
Reaction equation
IC.[Br:3][C:4]1[CH:9]=[C:8]([O:10][C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:6][C:5]=1[OH:15].[C:16](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.CCOCC>[Br:3][C:4]1[CH:9]=[C:8]([O:10][C:11]([F:13])([F:14])[F:12])[CH:7]=[CH:6][C:5]=1[O:15][CH3:16]Participants
Procedure
Iodomethane (14.94 mL, 0.24 mol) was added to a solution of 2-bromo-4-(trifluoromethoxy)phenol (Description 15, 7.2 g) and potassium carbonate (11.6 g, 0.084 mol) in dimethylformamide (60 mL) and the mixture was stirred at room temperature for 15 h. Water (400 mL) and ether (200 mL) were added and the layers were separated. The organic fraction was washed with water (4×200 mL), saturated aqueous sodium hydrogen carbonate (2×200 mL) and brine (200 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/EtOAc (100:0 increasing to 98:2), to give the title compound. 1H NMR (250 MHz, CDCl3) δ7.45 (1H, d, J 2.8 Hz), 7.16 (1H, dd, J 9.0, 2.8 Hz), 6.88 (1H, d, J 9.0 Hz), and 3.90 (3H, s).
Workup
- customthe layers were separated
- washThe organic fraction was washed with water (4×200 mL), saturated aqueous sodium hydrogen carbonate (2×200 mL) and brine (200 mL)
- dry with materialdried (MgSO4)
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by flash column chromatography on silica gel
- washeluting with hexane/EtOAc (100:0 increasing to 98:2)
Sources & evidence
- ORD record
- ord-e0cd0895a6284f66b656af309b803ee8
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06518273B1
Reaction notes
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