Sodium hydride → 2-Bromo-4-fluoro-1-(2,2,2-trifluoroethoxy)benzene
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].[F:10][C:11]([F:26])([F:25])[CH2:12]OC1C=C(S([O-])(=O)=O)C=CC=1C.[H-].[Na+]>CN(C)C=O.O>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:12][C:11]([F:26])([F:25])[F:10]Participants
6
Conditions
- Temperature
- 110 °C
Procedure
To a solution of 2-bromo-4-fluorophenol (4 g) and 2,2,2-trifluoroethoxy-p-toluene sulphonate (5 g) in dimethylformamide (40 ml) was slowly added sodium hydride (1 g, 60% in oil) and the mixture then heated at 110° C. for 12 h. The solution was cooled, diluted with water (500 ml) and the product extracted into ethyl acetate (2×150 ml). The organic phase was washed with saturated NaHCO3 solution, water, saturated brine and dried (MgSO4). The solvent was removed in vacuo and the residue was chromatographed on silica gel (eluting with diethyl ether/hexane (1:5)) to give the title compound as a colourless oil. 1H NMR (250 MHz, CDCl3) δ4.36 (2H, q, J 8 Hz), 6.91-7.05 (2H, m), and 7.33 (1H, dd, J 8, 3 Hz).
Workup
- temperatureThe solution was cooled
- extractionthe product extracted into ethyl acetate (2×150 ml)
- washThe organic phase was washed with saturated NaHCO3 solution, water, saturated brine
- dry with materialdried (MgSO4)
- customThe solvent was removed in vacuo
- customthe residue was chromatographed on silica gel (eluting with diethyl ether/hexane (1:5))
Sources & evidence
- ORD record
- ord-fb02bc958a1d445b876dd24eeb3f5726
- Source dataset
- uspto-grants-2000_06
- Patent number
- US06071927
Reaction notes
Loading…