Iodine → 2-iodobenzene-1,3-diol

Participants

Reaction Conditions

Reaction Steps

Add sodium bicarbonate (27.9 g, 333 mmol) to a solution of benzene-1,3-diol (33.0 g, 300 mmol), and iodine (81.5 g, 321 mmol) in water (225 mL) chilled to 0° C. and stir. Warm the solution to ambient temperature gradually over 1 hour. Extract with diethyl ether, combine organic layers, dry with sodium sulfate, filter and concentrate under reduced pressure to yield a white solid. Triturate the solid in chloroform (100 mL) chilled to −10° C. After 30 minutes, filter the precipitate, washing with cold chloroform to yield the title compound as a white solid (49.0 g, 69%): 1H NMR (DMSO-d6) δ 6.33 (d, 2H), 6.93 (t, 1H), 10.03 (s, 2H).

Provenance & Evidence