Bromine → 3,5-Dibromo-2-methoxypyridine
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.C([O-])(=O)C.[Na+].[Br:15]Br>C(O)(=O)C.O>[Br:15][C:4]1[C:5]([O:8][CH3:9])=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To 5-bromo-2-methoxypyridine (0.564 g, 3.0 mmol) and sodium acetate (0.246 g, 3.0 mmol) in acetic acid (3 mL) was added bromine (0.27 mL, 5.25 mmol), and the mixture was stirred at 80° C. for 3 hours, and then at room temperature overnight. The mixture was diluted with H2O and extracted with EtOAc, and the combined organic layers were washed with saturated aqueous Na2CO3 and saturated aqueous Na2S2O3. The organic layer was concentrated and dried under high vacuum to give 3,5-dibromo-2-methoxy-pyridine.
Workup
- customat room temperature
- customovernight
- extractionextracted with EtOAc
- washthe combined organic layers were washed with saturated aqueous Na2CO3 and saturated aqueous Na2S2O3
- concentrationThe organic layer was concentrated
- customdried under high vacuum
Sources & evidence
- ORD record
- ord-9cf0eb6a7aff46bc87c8765a8552bf59
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08049015B2
Reaction notes
Loading…