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

Temperature

80 °C

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).

1. customTo a round bottom flask was combined
2. temperatureThe solution was cooled to room temperature
3. concentrationconcentrated
4. dissolutionThe resulting residue was dissolved in ethyl acetate
5. additionan aqueous solution of sodium bisulfite was added
6. washThe organic layer was washed three times with water and brine
7. dry with materialdried over sodium sulfate
8. concentrationThe organic layer was concentrated to dryness
9. customrecrystallized from hexanes

ORD record

ord-19cd2b61e0ee4ec88e85931b82487d9f

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07709645B2