[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:5]=1.Cl[CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21]>C1COCC1.C(OCC)(=O)C>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])=[C:6]([C:11]([F:12])([F:13])[F:14])[CH:5]=1Sodium hydride (6.55 g) was added in small portions to a solution of 4-bromo-2-(trifluoromethyl)phenol (32.9 g) in THF (150 ml). After stirring at room temperature for 10 minutes, 1-(chloromethoxy)-2-methoxyethane (17 g) was then added by syringe. The mixture was stirred at room temperature for 24 hours then diluted with ethyl acetate (300 mL) and washed with water. Organics were dried over sodium sulphate and solvent evaporated under reduced pressure. The resulting residue was columned on silica gel using heptane as eluant to afford 4-bromo-1-((2-methoxy-ethoxy)methoxy)-2-(trifluoromethyl)benzene (78% yield).
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