Methanol → 4-Bromo-3-fluoro-2-methylbenzoic acid
Reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[F:11].O.[CH3:13]O>S(=O)(=O)(O)O>[CH3:13][C:4]1[C:3]([F:11])=[C:2]([Br:1])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
4-Bromo-3-fluorobenzoic acid (WAKO, 1.0 g) was dissolved in methanol (10 mL), followed by addition of concentrated sulfuric acid (10 drops). The mixture was refluxed for three hours. After cooling to room temperature, water was added and the extraction was carried out with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain the target compound (618 mg).
Workup
- temperatureThe mixture was refluxed for three hours
- extractionthe extraction
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- distillationthe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-299044bc3ba543eeba9f203ba863f82b
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08039514B2
Reaction notes
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