Methanol → Methyl 4-bromo-2-methylbenzoate

Participants

Reaction Steps

To a solution of 4-bromo-2-methyl-benzoic acid 10.0 g, 46.5 mmol) in methanol (100 mL) at room temperature was added sulfuric acid (conc. 1 mL) dropwise. The solution was heated at reflux for 16 h. The solution was removed from heat and sulfuric acid (conc. 0.5 mL) was added. The solution was heated at reflux 2 h then cooled to room temperature and concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate, then with saturated sodium chloride. The solution was dried (MgSO4), filtered, and concentrated in vacuo to a crude colorless oil. Flash chromatography (SiO2, 5% ethyl acetate/hexane) gave the title compound as a colorless oil (9.2 g, 87%). 1H NMR (400 MHz, CDCl3): δ ppm 2.58 (s, 3 H) 3.88 (s, 3 H) 7.38 (dd, J=8.46, 1.89 Hz, 1 H) 7.42 (d, J=1.52 Hz, 1 H) 7.78 (d, J=8.34 Hz, 1 H).

Provenance & Evidence