Bromine → 6-Bromo-2-nitropyridin-3-ol
Reaction equation
[OH:1][C:2]1[C:3]([N+:8]([O-:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C[O-].[Na+].[Br:14]Br>CO>[Br:14][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([N+:8]([O-:10])=[O:9])[N:4]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
3-Hydroxy-2-nitropyridine (20 g, 0.143 mole) was dissolved in methanol (400 ml) and a solution of 25% sodium methoxide in methanol (33 ml, 0.13 mole) was added at room temperature. The mixture was stirred for 30 min, then was cooled to 0° C., and bromine (7.2 ml, 0.14 mole) was added slowly. The reaction was then stirred at 0° C. for 30 min, then was quenched with glacial AcOH (2.5 ml). The solvent was removed in vacuo to afford material (30 g, 96%), which was used without further purification.
Workup
- stirringThe reaction was then stirred at 0° C. for 30 min
- customwas quenched with glacial AcOH (2.5 ml)
- customThe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-8e01353b988648b8b3ac93694dbe40d9
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07141564B2
Reaction notes
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