Benzyl Bromide → 1-[2-(Benzyloxy)ethyl]-3-iodobenzene

Participants

Reaction Steps

Into a 50-mL 3-necked round-bottom flask under N2 was placed a solution of 2-(3-iodophenyl)ethanol (470 mg, 1.90 mmol) in tetrahydrofuran (10 mL). Sodium hydride (91 mg, 3.8 mmol, 2 equiv.) was added at 0° C. The resulting mixture was warmed to room temperature and stirred at room temperature for 2 h. Benzyl bromide (272 μL, 3.9 mmol, 2.05 equiv.) and tetra-n-butylammonium bromide (61 mg, 0.19 mmol, 0.10 equiv.) were added at room temperature. The resulting solution was stirred for 20 h at room temperature. The reaction progress was monitored by TLC (EtOAc/petroleum ether 1:30). The reaction was then quenched by the addition of aqueous NH4Cl (10 mL). The resulting solution was extracted with EtOAc (3×60 mL), and the organic layers were combined and washed with brine (50 mL). The residue was chromatographed on silica gel with EtOAc/petroleum ether 1:20 to give 0.48 g (75%) of 1-[2-(benzyloxy)ethyl]-3-iodobenzene as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 7.62 (s, 1H), 7.58 (d, 1H, J=7.8 Hz), 7.42-7.25 (m, 5H), 7.22 (d, 1H, J=7.8 Hz), 7.05 (t, 1H, J=7.8 Hz), 4.55 (s, 2H), 3.69 (t, 2H, J=6.9 Hz), 2.89 (t, 2H, J=6.9 Hz).

Provenance & Evidence