Methanol → Methyl 3-iodo-4-methylbenzoate

Temperature

60 °C

To a solution of 3-iodo-4-methylbenzoic acid (28.0 g, 0.107 mol) in MeOH (300 mL) at 0° C. was carefully added concentrated H2SO4 (30 mL). The mixture was heated at 60° C. overnight, then cooled and the solvent removed under reduced pressure. The residue was carefully poured onto ice-water (200 mL) and the mixture was extracted with EtOAc (500 mL). The organics was washed with water (100 mL), saturated NaHCO3 (100 mL), brine (100 mL), dried (MgSO4), filtered, and concentrated to yield the title compound as a brown oil (29.0 g, 98%). 1H NMR (400 MHz, CDCl3) δ 8.47 (d, J=1.7 Hz, 1H), 7.90 (dd, J=7.9 Hz, 1.7 Hz, 1H), 7.29 (d, J=7.9 Hz, 1H), 3.90 (s, 2H), 2.48 (s, 3H).

1. temperaturecooled
2. customthe solvent removed under reduced pressure
3. additionThe residue was carefully poured onto ice-water (200 mL)
4. extractionthe mixture was extracted with EtOAc (500 mL)
5. washThe organics was washed with water (100 mL), saturated NaHCO3 (100 mL), brine (100 mL)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-49bc2be8317140c5baaa6f7cf061b8fd

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428502B2