Methanol → Methyl 5-bromo-2-hydroxy-4-methylbenzoate

Temperature

70 °C

To a solution of 5-bromo-2-hydroxy-4-methylbenzoic acid (6.78 g) in methanol (200 mL) was added dropwise sulfuric acid (6.77 mL), and the mixture was stirred overnight at 70° C. The reaction mixture was concentrated under reduced pressure, the residue was neutralized with saturated aqueous sodium bicarbonate solution under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (6.56 g).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. temperaturecooling
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic layer was washed with water and saturated brine
5. dry with materialdried over anhydrous sodium sulfate
6. customthe solvent was evaporated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

ORD record

ord-f0aa6ed699214ee5bf00a9caa14208ca

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09315458B2