Methanol → Methyl 4-bromo-2-methylbenzoate

4-Bromo-2-methylbenzoic acid (75.0 g) was dissolved in methanol (500 ml) and concentrated sulfuric acid (10 ml) was added. The mixture was heated at reflux for 20 hrs. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. Water (150 ml) was added to the obtained residue, and the mixture was extracted with ethyl acetate (150 ml). The organic layer was washed successively with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure to give the title compound (78.0 g).

1. temperatureThe mixture was heated
2. temperatureat reflux for 20 hrs
3. concentrationconcentrated under reduced pressure
4. additionWater (150 ml) was added to the obtained residue
5. extractionthe mixture was extracted with ethyl acetate (150 ml)
6. washThe organic layer was washed successively with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated under reduced pressure

ORD record

ord-4f9f75db62864ac59c08cb3e8978ddbe

Source dataset

uspto-grants-2007_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07304174B2