Chlorosuccinimide → Methyl 2-amino-3-chloro-5-iodobenzoate

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask was combined 1.00 g (3.61 mmol) of 2-amino-5-iodo-benzoic acid methyl ester and 18.0 mL isopropyl alcohol. To the solution was added 541 mg (4.05 mmol) of N-chlorosuccinimide and the solution was heated at 80° C. in an oil bath for 2.25 hours. The solution was cooled to room temperature and concentrated. The resulting residue was dissolved in ethyl acetate and an aqueous solution of sodium bisulfite was added. The organic layer was washed three times with water and brine, then dried over sodium sulfate. The organic layer was concentrated to dryness and recrystallized from hexanes to afford 809 mg (2.60 mmol, 72% yield) of 2-amino-3-chloro-5-iodo-benzoic acid methyl ester as tan-orange crystals. 1H NMR (500 MHz, DMSO-d6) δ 7.96 (d, 1H), 7.74 (d, 1H), 6.86 (s, br., 2H), 3.82 (s, 3H).

Provenance & Evidence