Methanol → Methyl 2-fluoro-3-methylbenzoate

To a solution of 2-fluoro-3-methyl benzoic acid (3.57 g, 23 mmol) in MeOH (40 mL) was added concentrated sulfuric acid (2.3 mL), and the reaction mixture was heated at reflux for 12 h. The reaction mixture was cooled, the solvent was removed under reduced pressure, and the residue was dissolved in EtOAc. The organic solution was washed with a saturated solution of NaHCO3 and then brine, dried (Na2SO4), filtered and concentrated under reduced pressure to afford methyl 2-fluoro-3-methylbenzoate as a yellow oil (3.2 g, 82%): 1H NMR (300 MHz, CDCl3) δ 7.76-7.71 (m, 1H), 7.39-7.34 (m, 1H), 7.08 (t, J=8 Hz, 1H), 3.98 (s, 3H), 2.31 (d, J=3 Hz, 3H).

1. temperaturethe reaction mixture was heated
2. temperatureat reflux for 12 h
3. temperatureThe reaction mixture was cooled
4. customthe solvent was removed under reduced pressure
5. dissolutionthe residue was dissolved in EtOAc
6. washThe organic solution was washed with a saturated solution of NaHCO3
7. dry with materialbrine, dried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORD record

ord-c25ab97eb0c14ab7b715bb84c82bfce9

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07067540B2