N-Iodosuccinimide → Methyl 2-amino-5-bromo-3-iodobenzoate

Participants

Reaction Steps

1-Iodo-pyrrolidine-2,5-dione (10.35 g, 46.0 mmol) was added in one portion to a solution of methyl 2-amino-5-bromo-benzoate (10.35 g, 45.0 mmol) in trifluoroacetic acid (90 mL) at ambient temperature. The reaction was stirred for about 1 hour at ambient temperature then concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (150 mL), washed with saturated Na2CO3 solution (2×150 mL) and a 10% aqueous solution of Na2S2O4 (2×100 mL), dried over anhydrous MgSO4, filtered and concentrated to yield methyl 2-amino-5-bromo-3-iodo-benzoate (15.5 g, 97%) as a yellow solid; RP HPLC (Table 1, Method e) Rt=2.45, 1H NMR (DMSO-d6, 400 MHz) δ 3.83 (s, 3H), 7.74 (broad s), 2H), 7.86-7.88 (d, 2H), 8.00-8.02 (d, 1H).

Provenance & Evidence