Methanol → Methyl 3-bromo-4-hydroxybenzoate
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:17]O>>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([O:7][CH3:17])=[O:6]Participants
4
Conditions
- Temperature
- 80 °C
Procedure
To a stirred solution of 3-bromo-4-hydroxybenzoic acid (C.1) (available from Alfa Aesar, Avocado, Lancaster) (50.0 g, 231 mmol) in MeOH (300 mL) was added a cold solution of sulfuric acid (2.50 mL, 47 mmol). The mixture was heated to 80° C. and monitored by TLC. After 16.5 hours, the solvent was removed and the reaction mixture was diluted with EtOAc. The organic phase was washed carefully two times with saturated aqueous NaHCO3, once with brine, and then dried over anhydrous sodium sulfate. After filtration, the organic solvent was removed in vacuo to yield C.2 as a white solid (yield 100%) that was used without purification.
Workup
- customthe solvent was removed
- additionthe reaction mixture was diluted with EtOAc
- washThe organic phase was washed carefully two times with saturated aqueous NaHCO3
- dry with materialonce with brine, and then dried over anhydrous sodium sulfate
- filtrationAfter filtration
- customthe organic solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-5f4e8b886014458cab8806d146d9140e
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450522B2
Reaction notes
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