Iodine → Methyl 2-amino-5-fluoro-3-iodobenzoate

Participants

Reaction Steps

Iodine (3.6 g, 14.2 mmol) was added to a mixture of methyl 2-amino-5-fluorobenzoate (2.4 g, 14.2 mmol), silver sulfate (4.42 g, 14.2 mmol) and ethanol (30 mL) at room temperature. The mixture was stirred under nitrogen for 1 h, and then quenched with a saturated solution of sodium bicarbonate, extracted with ethyl acetate. The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. The crude material was purified by column chromatography (silica gel, 90:10 hexanes/ethyl acetate) to afford methyl 2-amino-5-fluoro-3-iodobenzoate (3.9 g, 93%) as a light yellow solid: 1H NMR (300 MHz, CDCl3) δ 7.66-7.58 (m, 2H), 6.21 (br s, 2H), 3.89 (s, 3H); 19F NMR (282 MHz, CDCl3) δ 127.87; MS (ESI+) m/z 296 (M+H).

Provenance & Evidence