Iodine → 3-Acetoxy-2,4-dimethoxy-iodobenzene

Participants

Reaction Steps

To an ice-cooled suspension of acetic acid 2,6-dimethoxy-phenyl ester (1.0 g, 5.1 mmol) and silver triflouroacetate (5.1 mmol) in CHCl3 (16 ml) was added iodine (1.3 g, 5.1 mmol) and the reaction stirred for 1 hour. The crude mixture was filtered through celite to remove the precipitated silver iodide and the filtrate was washed with 10% Na2S2O3(aq). An emulsion was formed and the mixture was again passed through celite and the filtrate washed with brine, dried over MgSO4 and concentrated under reduced pressure to give the product as a tan solid (1.57 g, 96%). 1H-NMR (300 MHz, CDCl3) δ 7.55 (d, J=8.9 Hz, 1H), 6.54 (d, J=8.9 Hz, 1H), 3.80 (s, 6H), 2.33 (s, 3H).

Provenance & Evidence