Methanol → Methyl 4-bromo-2-nitrobenzoate

To a methanol solution (50 ml) of 4-bromo-2-nitrobenzoic acid (2.54 g) was added concentrated sulfuric acid (1.0 ml), followed by heating at reflux for 4 hours. The reaction solution was concentrated under reduced pressure, and water (20 ml) was added to the residue. Under ice cooling, 5 N aqueous sodium hydroxide solution (2.0 ml) and a saturated aqueous sodium hydrogen carbonate solution were added, and extracted with dichloromethane. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to afford methyl 4-bromo-2-nitrobenzoate (619 mg).

1. temperatureby heating
2. temperatureat reflux for 4 hours
3. concentrationThe reaction solution was concentrated under reduced pressure, and water (20 ml)
4. additionwas added to the residue
5. additionUnder ice cooling, 5 N aqueous sodium hydroxide solution (2.0 ml) and a saturated aqueous sodium hydrogen carbonate solution were added
6. extractionextracted with dichloromethane
7. washThe organic layer was washed with saturated sodium chloride solution
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe resulting residue was purified by silica gel column chromatography

ORD record

ord-816c60bda2c046deb2abda29e4b52a1f

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08729095B2