Iodine → HCID 18782545, compound

Participants

Reaction Steps

Iodine (21. g, 84 mmol) was added to a solution of 4-cyanophenol (10.0 g, 84 mmol) and sodium hydrogen carbonate (7.06 g, 84 mmol) in water (100 mL) and the mixture was stirred at room temperature for 24 h. The solid was collected, washed with water and dried in vacuo. The solid was dissolved in tetrahydrofuran (100 mL) and triphenylphosphine (14.4 g, 55 mmol) and 4-methoxybenzyl alcohol (8.3 g, 60 mmol) were added. Diethyl azodicarboxylate (8.5 mL, 55 mmol) was added slowly and the mixture was stirred at room temperature for 16 h. The mixture was poured into sodium hydrogen carbonate solution (saturated, 200 mL) and extracted with ethyl acetate (2×200 mL). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel to give the title compound (3.38 g). 1H NMR (250 MHz, CDCl3) δ 8.05 (1H, d, J 2.0 Hz), 7.57 (1H, dd, J 2.0, 8.5 Hz), 7.38 (2H, d, J 6.8 Hz), 6.79-6.96 (3H, m), 5.14 (2H, s), and 3.82 (3H, s).

Provenance & Evidence