Methyl iodide → Methyl 3-Bromo-2-methylbenzoate

Temperature

60 °C

A mixture of 3-bromo-2-methylbenzoic acid (16 g, 74.4 mmol), sodium bicarbonate (12.5 g, 148.8 mmol) and iodomethane (21.2 g, 148.8 mmol) in DMF (160 mL) was heated at 60° C. for 2 hours. The mixture was cooled to room temperature and poured into ice water (400 mL). The mixture was extracted with ethyl acetate (4×100 mL). The EtOAc solution was washed with water (3×100 mL), brine (100 mL) and dried (MgSO4). Solvent was removed to give methyl 3-bromo-2-methylbenzoate (17.6 g, 100%) as an oil: 1H NMR (CDCl3) δ 7.70 (t, J=7.6 Hz, 2H), 7.08 (t, J=7.9 Hz, 1H), 3.90 (s, 3H), 2.67 (s, 3H).

1. temperatureThe mixture was cooled to room temperature
2. extractionThe mixture was extracted with ethyl acetate (4×100 mL)
3. washThe EtOAc solution was washed with water (3×100 mL), brine (100 mL)
4. dry with materialdried (MgSO4)
5. customSolvent was removed

ORD record

ord-515a075d965b456ab2907b2f8edaf345

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07091353B2