Iodine → HCID 44419910, compound

Participants

Reaction Steps

To a solution of methyl (4-methoxyphenyl)acetate (1 mL, 6.3 mmol) in MeOH (40 mL) was added Ag2SO4 (1.96 g, 6.3 mmol) followed by I2 (1.6 g, 6.3 mmol). The reaction was stirred vigorously at room temperature for 1 hour and then the solids were removed by filtration. The filtrate was diluted with EtOAc (200 mL), and washed with aq. NaHSO3 (2×50 mL) and brine (2×50 mL). The organic layer was dried over Na2SO4, filtered, and concentrated to afford methyl (3-iodo-4-methoxyphenyl)acetate. Rf=0.27 (15% EtOAc/hexanes). 1H NMR (500 MHz, CDCl3) δ 7.68 (d, J=2.0 Hz, 1H), 7.21 (dd, J=8.2, 1.8 Hz, 1H), 6.76 (d, J=8.4 Hz, 1H), 3.85 (s, 3H), 3.68 (s, 3H), 3.52 (s, 2H).

Provenance & Evidence