Sodium Iodide → HCID 20090642, compound

Participants

Reaction Steps

To all of the above benzyl chloride in acetone (30 mL) is added sodium iodide (1.70 g., 10.0 mmol, 2.90 equiv.) and potassium carbonate (0.450 g., 10.5 mmol, 3.04 equiv.). The mixture is allowed to stir for 18 hours at room temperature. The solvents are evaporated, and the residue extracted twice with EtOAc. The extracts are washed with water and then brine. The organic phase is dried (MgSO4), and concentrated to afford 4-[1-adamantyl]-3-methoxybenzyl iodide (18b) (1.10 g., 2.88 mmol, 84%): mp=143°-144° C.; 1H NMR (300 MHz, CDCl3) δ 7.25 (d, J=7 Hz, 1H, ArH), 6.95 (d, J=7 Hz, 1H, ArH), 6.85 (s, 1H, ArH), 4.46 (s, 2H, ArCH2I), 3.85 (s, 3H, OCH3), 2.07 (s, 9H, adamantyl), 1.77 (s, 6H, adamantyl) .

Provenance & Evidence