Acetic Anhydride → N-(4-Iodophenyl)acetamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-iodoaniline (20.00 g, 90.0 mmol, 1.0 equiv) triethylamine (38.4 ml, 274 mmol, 3.0 equiv) and CH2Cl2 (200 ml) was cooled to 0° C. Acetic anhydride (26.0 ml, 270 mmol, 3.0 equiv) was added drop wise. The reaction mixture was stirred at 0° C. for 10 min, and at rt for 2 h. The volatile materials were removed under vacuum, and the solid residue was dissolved in 30 ml of hot CH2Cl2. The solution was left to stand in a freezer for 72 h. The separated solid was filtered out and dried under vacuum to give N-(4-iodophenyl)acetamide (20.35 g, 86.6%). 1H NMR (CDCl3) δ 7.58–7.28 (d, 2H), 7.25–7.23 (d, 2H), 2.15 (s, 3H).

Provenance & Evidence