Phenol → HCID 19384988, compound

Participants

Reaction Steps

4-Acetamido-3,5-dichlorobenzenediazonium tetrafluoroborate was converted to the corresponding phenol according to the procedure of T. Cohen, et. al., J. Org. Chem., 42, 2053-2058 (1977). Thus, 22 g (94 rnmol) of copper (II) nitrate was dissolved in 100 mL of water and 300 mg (0.94 mmol) of 4-acetamido-3,5-dichlorobenzenediazonium tetrafluoroborate was added. Copper (I) oxide (405 mg, 2.8 mmol) was added. The mixture was stirred for 35 min, then filtered through Celite, diluted with 1N aqueous sodium bisulfate, and extracted with 4 portions of dichloromethane and 8 portions of ethyl acetate. The combined organic phases were dried over magnesium sulfate and concentrated. Purification by flash chromatography (silica, 50% ethyl acetate/hexanes) gave 72 mg (35%)of 4-acetamido-3,5-dichlorophenol. This compound was convened to the title compound in a manner analogous to that of Example 1: 1H NMR (400 MHz, CDCl3) δ6.97 (s, 2H), 4.21 (dd, 1H), 3.86 (dd, 1H), 3.32 (m, 1H), 2.91 (t, 1H), 2.73 (dd, 1H), 2.20 (s, 3H).

Provenance & Evidence