Diisopropyl diisopropyl diisopropyl-1,2-dicarboxylate (1.56 g, 7.34 mmol) was slowly added dropwise to a solution of THF (20 mL) containing 3-bromophenol (1.155 g, 6.68 mmol), 2-(dimethylamino)ethanol (0.65 g, 7.34 mmol) and triphenylphosphine (1.93 g, 7.34 mmol) at 0 °C. The reaction mixture was gradually warmed to room temperature over a period of 16 h. The volatiles were subsequently removed by distillation under reduced pressure. The residue was dissolved in ethyl acetate (20 mL) and extracted with 1N HCl (20 mL), the aqueous phase was retained and washed with ethyl acetate. The aqueous phase was subsequently neutralized with saturated NaHCO3 solution (50 mL), extracted again with ethyl acetate, and the organic phase was dried over anhydrous MgSO4. Finally, the target product 2-(3-bromophenoxy)-N,N-dimethylethylamine (1.03 g, 63% yield) was purified by silica gel column chromatography (eluent: 4% MeOH/DCM) as an oil.
