Methanol → Methyl 4-chloro-3-iodobenzoate

Temperature

80 °C

4-Chloro-3-iodo-benzoic acid (5.31 g, 18.8 mmol) was dissolved in methanol (50 mL) and concentrated sulfuric acid (3 mL) was carefully added. The solution was stirred at 80° C. for 4 hours, then cooled to room temperature and the volatile organics were removed under reduced pressure. The residue was partitioned between EtOAc (50 mL) and water (50 mL) and the organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2; 0-10% EtOAc in hexanes) to yield 5.32 g (95%) of the title compound as an oil. 1H NMR (400 MHz, Chloroform-d) δ 8.54 (d, J=2.0 Hz, 1H), 7.96 (dd, J=8.4, 2.0 Hz, 1H), 7.53 (d, J=8.4 Hz, 1H), 3.94 (s, 3H).

1. temperaturecooled to room temperature
2. customthe volatile organics were removed under reduced pressure
3. customThe residue was partitioned between EtOAc (50 mL) and water (50 mL)
4. washthe organic layer was washed with brine
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by flash chromatography (SiO2; 0-10% EtOAc in hexanes)

ORD record

ord-629d46e0a6254166a7b132c2622b490a

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428502B2