[Br:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[OH:13].C(=O)([O-])[O-].[K+].[K+].I[CH2:21][CH3:22].O>CN(C)C=O.C(OCC)(=O)C>[CH2:21]([O:13][C:3]1[CH:4]=[CH:5][C:6]([O:8][C:9]([F:11])([F:12])[F:10])=[CH:7][C:2]=1[Br:1])[CH3:22]2-Bromo-4-trifluoromethoxyphenol (Description 11, 1 g) was dissolved in N,N dimethylformamide (12 ml) and potassium carbonate (1.07 g) was added. Iodoethane (0.78 ml) was added and the mixture was stirred at room temperature. Water (150 ml) and ethyl acetate were added and the layers were separated. The organic layer was washed with brine, 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 95:5) to give the title compound as a colourless oil (1.02 g). 1H NMR (250 MHz, CDCl3) δ1.47 (3 H, t, J 7.0 Hz), 4.09 (2 H, q, J 7.0 Hz), 6.85 (1 H, d, J 9.0 Hz), 7.11 (1 H, m), and 7.43 (1 H, m).
Loading…
