Diethyl Ether → 1-(3-Bromopyridin-4-yl)ethanol
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]=[O:9].[CH3:10][Mg]Br.CCOCC.[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]([OH:9])[CH3:10]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
To a cooled (0° C.) solution of 3-bromo-pyridine-4-carbaldehyde (2.0 g, 10.8 mmol) in dry THF (45 mL) is added methyl magnesium bromide solution in Et2O (3M; 3.9 mL, 11.8 mmol). The mixture is stirred at 0° C. for 1 h then warmed and stirred at room temperature for 1 h. Saturated aqueous NH4Cl solution is added and the mixture is extracted with EtOAc. The organic layers are combined and concentrated to afford 2.1 g of 1-(3-bromo-pyridin-4-yl)-ethanol.
Workup
- temperaturethen warmed
- stirringstirred at room temperature for 1 h
- extractionthe mixture is extracted with EtOAc
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-40dbab02ed7f43e985c7d559cb9f341e
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181272B2
Reaction notes
Loading…