Methanol → Methyl 3-amino-6-bromo-2-methylbenzoate
Reaction equation
[NH2:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].CO.[Br:15]Br>C(O)(=O)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>[NH2:1][C:2]1[C:3]([CH3:12])=[C:4]([C:9]([Br:15])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]Participants
Procedure
To a mixture of methyl 3-amino-2-methylbenzoate (5.00 mL, 34.7 mmol) in acetic acid (100 mL)-methanol (200 mL) was added bromine (5.55 g, 34.7 mmol) under ice-cooling, and the mixture was stirred for 5 min. The reaction solution was diluted with saturated aqueous sodium thiosulfate solution, and the organic solvent was evaporated under reduced pressure. The residual aqueous solution was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with 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=5/95→20/80) to give the title compound (4.66 g, yield 55%).
Workup
- temperaturecooling
- customthe organic solvent was evaporated under reduced pressure
- additionThe residual aqueous solution was diluted with saturated aqueous sodium hydrogen carbonate solution
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95→20/80)
Sources & evidence
- ORD record
- ord-91383f919407435f8df3d10266d830e1
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08110585B2
Reaction notes
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