Step 1: Synthesis of 1-bromo-4-ethoxybenzene: Potassium carbonate (118 g) was added to a solution of 4-bromophenol (50 g) in acetone (250 mL) at room temperature and stirred for 30 min. Subsequently, iodoethane (67.6 g) was added slowly and dropwise. The reaction mixture was heated to reflux for 10 hours and the progress of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the mixture was filtered and acetone was removed using a rotary evaporator. The residue was dissolved in ethyl acetate, washed sequentially with water and saturated brine, dried over anhydrous sodium sulfate and concentrated. Purification by silica gel column chromatography with ethyl acetate and hexane (1:7) as eluents afforded 4-bromophenetole as a colorless liquid (57 g, 98.27% yield).1H NMR (CDCl3, 300 MHz): δ 7.35 (d, J = 8.7 Hz, 2H), 6.76 (d, J = 8.7 Hz, 2H), 3.99 (q, J = 6.9 Hz, 2H), 1.40 (t, J = 6.9 Hz, 3H).
