The general procedure for the synthesis of 4-iodophenylethyl ether from ethyl bromide and 4-iodophenol was as follows: 233.50 g (1.06 mol) of 4-iodophenol and 42.45 g (1.06 mol) of sodium hydroxide were ground to a powder in a dry mortar and pestle, and the mixture was subsequently transferred to a 1000 mL round-bottomed flask equipped with a magnetic stirrer. To the flask was added 300 mL of ethylene bromide, 15 mL of N,N-dimethylformamide and a catalytic amount of cesium hydroxide. The reaction mixture was stirred at room temperature for 1 hour and then gradually heated to 80 °C and refluxed for about 70 hours. Complete consumption of the reaction starting material was confirmed by thin layer chromatography (TLC). After the reaction solution was cooled to room temperature, the solvent ethyl bromide was removed by evaporation under reduced pressure. Subsequently, appropriate amounts of dichloromethane and water were added sequentially under stirring, the organic layer was separated, dried with anhydrous magnesium sulfate, filtered and concentrated to give 252.43 g of a red oily product in 96.2% yield. The structure of the product was characterized by 1H NMR, IR and HRMS: 1H NMR (400 MHz, (CD3)2SO) δ 7.57 (d, J = 8.8 Hz, 2H), 6.76 (d, J = 8.8 Hz, 2H), 3.98 (q, J = 6.9 Hz, 2H), 1.30 (t, J = 7.0 Hz, 3H); IR (KBr , cm-1) 2979, 2929, 1586, 1486, 1392, 1244, 1047, 820, 630, 507; HRMS (GCT-MS) calculated value C8H9IO [M+] 247.97, measured value 247.9692.
