Methanol → Methyl 2-(3-bromophenyl)acetate

To a solution of 2-(3-bromophenyl) acetic acid (30 g, 0.14 mol) in CH3OH (200 mL) was added a catalytic amount of H2SO4. The mixture was heated at reflux for 6 h. The reaction mixture was allowed to cool to room temperature and the solvent was evaporated under reduced pressure. The residue was diluted with ethyl acetate (200 mL), which was washed with saturated aqueous Na2CO3, water and brine. The solution was dried over Na2SO4, filtered and concentrated under reduced pressure to give methyl 2-(3-bromophenyl)acetate (22 g, 69%). 1H NMR (CDCl3, 300 MHz) δ 7.44 (s, 1H), 7.42-7.38 (m, 1H), 7.21-7.19 (m, 2H), 3.70 (s, 3H), 3.59 (s, 2H).

1. temperatureThe mixture was heated
2. temperatureat reflux for 6 h
3. customthe solvent was evaporated under reduced pressure
4. additionThe residue was diluted with ethyl acetate (200 mL), which
5. washwas washed with saturated aqueous Na2CO3, water and brine
6. dry with materialThe solution was dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-5ec2e0b7338d4f7fb293a98e1461ba44

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07659268B2