Ethanol → 3,6-Dibromopyridine-2-carbaldehyde
Reaction equation
[Br:1][C:2]1[C:3]([CH:9](Br)Br)=[N:4][C:5]([Br:8])=[CH:6][CH:7]=1.CC[OH:14]>O.[N+]([O-])([O-])=O.[Ag+]>[Br:1][C:2]1[C:3]([CH:9]=[O:14])=[N:4][C:5]([Br:8])=[CH:6][CH:7]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A solution of silver nitrate (8.5 g, 50 mmol) in water (26 mL) was added dropwise to a solution of compound 84 (8.17 g, 20 mmol) in refluxing EtOH (100 mL). The mixture was stirred at 80° C. for 5 hours. After the mixture was cooled to room temperature, it was diluted with water (100 mL), extracted with EtOAc (3×), dried over Na2SO4, filtered and concentrated under reduced pressure. The product was obtained after silica gel chromatography eluting with 0-40% EtOAc in hexane (2.85 g, 51% over two steps).
Workup
- temperatureAfter the mixture was cooled to room temperature
- extractionextracted with EtOAc (3×)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe product was obtained after silica gel chromatography
- washeluting with 0-40% EtOAc in hexane (2.85 g, 51% over two steps)
Sources & evidence
- ORD record
- ord-770831a3eb274f6183db94c0cbf2fca2
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08283358B2
Reaction notes
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