Methanol → Methyl 4-bromo-2-methylbenzoate

4-Bromo-2-methylbenzoic acid (4.06 g, 18.5 mmol) was dissolved in methanol (60 ml). The solution was added with concentrated sulfuric acid (1 ml), and then heated under reflux for 9 hours. The solvent was evaporated under reduced pressure, and the residue was diluted with ethyl ether (100 ml). The resulting dilution was washed with water, an aqueous sodium bicarbonate solution, and then with saturated brine, and dried over magnesium sulfate. Insoluble solids were removed by filtration, and the filtrate was concentrated under reduced pressure to obtain the tile compound as yellow oil (3.87 g, yield: 91%).

1. temperatureheated
2. temperatureunder reflux for 9 hours
3. customThe solvent was evaporated under reduced pressure
4. additionthe residue was diluted with ethyl ether (100 ml)
5. washThe resulting dilution was washed with water
6. dry with materialan aqueous sodium bicarbonate solution, and then with saturated brine, and dried over magnesium sulfate
7. customInsoluble solids were removed by filtration
8. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-327720965db5416dba332f6bc07700b3

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07166617B2