Methyl iodide → 1-Iodo-4-(2-methoxyethyl)benzene

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Sodium hydride (60% dispersion in mineral oil, 612 mg, 15.3 mmol) was slowly added to a solution of 4-iodophenethyl alcohol (2.53 g, 10.2 mmol) in THF (12 mL) at room temperature and with stirring. At the end of the addition, the solution had become cloudy. The reaction mixture was heated to 60° C. for 2 h and then cooled to 0° C. Iodomethane (952 μL, 15.3 mmol) was slowly added to the solution and the reaction mixture was stirred overnight. Upon the completion of the reaction, the mixture was cooled to 0° C., neutralized with aq. sat. NH4Cl (25 mL) and extracted with EtOAc (3×25 mL). The combined extracts were sequentially washed with aq. sat. NH4Cl (3×20 mL), brine (20 mL) and dried (Na2SO4). The crude product was concentrated and dried over high vacuum. Chromatography of the residue (EtOAc/hexanes=1/5) gave 2.39 g (9.12 mmol) of the title product. Yield: 89%, pale yellow oil. 1H NMR (300 MHz, CDCl3): δ 7.61 (d, J=8.2 Hz, 2H), 6.98 (d, J=8.2 Hz, 2H), 3.57 (t, J=6.8 Hz, 2H), 3.34 (s, 3H), 2.82 (t, J=6.8 Hz, 2H) ppm. 13C NMR (75 MHz, CDCl3): δ 138.9, 137.5, 131.1, 91.6, 73.3, 58.9, 35.9 ppm.

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