Potassium Hydroxide → 3-Bromo-1-benzofuran-5-carbaldehyde
Reaction equation
Br[CH:2]1[CH:6]([Br:7])[C:5]2[CH:8]=[C:9]([CH:12]=[O:13])[CH:10]=[CH:11][C:4]=2[O:3]1.[OH-].[K+]>C(O)C.O>[Br:7][C:6]1[C:5]2[CH:8]=[C:9]([CH:12]=[O:13])[CH:10]=[CH:11][C:4]=2[O:3][CH:2]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 2,3-dibromo-2,3-dihydro-1-benzofuran-5-carbaldehyde (4.1 g) in dry ethanol (15 mL) was added a solution of KOH (2.2 eq.) in dry ethanol (14 mL) and refluxed at 70° C. for 1 h. The reaction mixture was cooled, diluted with water and extracted with EtOAc (3×50 mL). The organic layer was washed with water, brine and dried. The solvent was removed under vacuum and the residue was purified by flash chromatography (pet. ether/EtOAc 99.5:0.5) to give the title compound as a pale yellow solid (2.91 g (80% pure), yield=78%).
Workup
- temperatureThe reaction mixture was cooled
- extractionextracted with EtOAc (3×50 mL)
- washThe organic layer was washed with water, brine
- customdried
- customThe solvent was removed under vacuum
- customthe residue was purified by flash chromatography (pet. ether/EtOAc 99.5:0.5)
Sources & evidence
- ORD record
- ord-536903aa5f574ebc9f6f46b5770fc5cd
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07846925B2
Reaction notes
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