Acetaldehyde → 1-(3,5-Dibromopyridin-4-yl)ethanol
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[Li+].CC([N-]C(C)C)C.[CH:17](=[O:19])[CH3:18].[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[C:7]=1[CH:17]([OH:19])[CH3:18]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a cooled (−78° C.) solution of 3,5-dibromo-pyridine (2.0 g, 8.4 mmol) in dry THF (80 mL) is added LDA in THF solution (2M; 5.1 mL, 10.1 mmol) and the mixture is stirred at −78° C. for 2 h. Acetaldehyde in THF solution (5M; 3.4 mL, 16.9 mmol) is added and the mixture is stirred at −78° C. for 30 min, then at room temperature for 16 h. Saturated aqueous NH4Cl solution is added and the mixture is extracted with EtOAc. The organic layers are combined and concentrated to give the crude product. Purification by flash column chromatography affords 2.9 g (67% purity) of 1-(3,5-dibromo-pyridin-4-yl)-ethanol.
Workup
- stirringthe mixture is stirred at −78° C. for 30 min
- waitat room temperature for 16 h
- extractionthe mixture is extracted with EtOAc
- concentrationconcentrated
- customto give the crude product
- customPurification by flash column chromatography
Sources & evidence
- ORD record
- ord-94da2646746c43a48491731164f96134
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181272B2
Reaction notes
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