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 (7.6 g, 45 mmol) in water (24 mL) was added dropwise to a solution of 42A (7.36 g, 18 mmol) in refluxing EtOH (90 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 times), dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product (42B, 4.6 g) was directly used for next step. MS (m/z): 265.96. [M+H]+
Workup
- temperatureAfter the mixture was cooled to room temperature
- extractionextracted with EtOAc (3 times)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-fb6116aa5225427d82163ab0348b4d57
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09050344B2
Reaction notes
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