Isopropanol → 5-Bromo-3-chloro-2-[(propan-2-yl)oxy]pyridine
Reaction equation
[CH3:1][C:2](C)([O-:4])[CH3:3].[K+].CC(O)C.[Br:11][C:12]1[CH:13]=[C:14]([Cl:19])[C:15](Cl)=[N:16][CH:17]=1>>[Br:11][C:12]1[CH:13]=[C:14]([Cl:19])[C:15]([O:4][CH:2]([CH3:3])[CH3:1])=[N:16][CH:17]=1Participants
4
Conditions
- Temperature
- 95 °C
Procedure
Potassium tert-butoxide (25.7 g, 229 mmol) was added to 2-propanol (100 mL, 57.3 mmol) and the solution was stirred at 95° C. for 3 h, then 5-bromo-2,3-dichloropyridine (13 g, 57.3 mmol) was added. This reaction was refluxed overnight. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and water. The organic phase was washed with water and saturated brine, dried over sodium sulphate and evaporated in vacuo to afford the crude product 5-bromo-3-chloro-2-[(1-methylethyl)oxy]pyridine (D107) (14.5 g), which was used directly without further purification.
Workup
- temperatureThis reaction was refluxed overnight
- temperatureThe reaction mixture was cooled to room temperature
- custompartitioned between ethyl acetate and water
- washThe organic phase was washed with water and saturated brine
- dry with materialdried over sodium sulphate
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-e484f019ca7e4b03ba5fd92bb648e3c8
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08389508B2
Reaction notes
Loading…