Methanol → Methyl 5-amino-2-bromobenzoate
Reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Br:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].OS(O)(=O)=O.[CH3:17]O>>[CH3:17][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([NH2:1])[CH:3]=[CH:4][C:5]=1[Br:11]Participants
4
Procedure
5-Amino-2-bromobenzoic acid (10.8 g, 50 mmol) was dissolved in methanol (100 mL). Conc. H2SO4 (2 mL) was added slowly and the reaction mixture heated to reflux for 4 h. The mixture was concentrated and the residue was allowed to cool to room temperature. It was poured over crushed ice. The organic product was extracted using diethyl ether (2×200 mL). The organic extract was washed with water, 10% aqueous NaHCO3, dried (anhydrous Na2SO4) and concentrated to get the title compound.
Workup
- temperaturethe reaction mixture heated
- temperatureto reflux for 4 h
- concentrationThe mixture was concentrated
- additionIt was poured
- customover crushed ice
- extractionThe organic product was extracted
- extractionThe organic extract
- washwas washed with water, 10% aqueous NaHCO3
- dry with materialdried (anhydrous Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f1c317c4064d4caba2b081794b5ef3de
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07884127B2
Reaction notes
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