Water → 5-Bromo-2-chloro-3-nitropyridine
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](O)=[N:6][CH:7]=1.O.C(=O)(O)[O-].[Na+].P(Cl)(Cl)([Cl:20])=O>>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([Cl:20])=[N:6][CH:7]=1Participants
5
Conditions
- Temperature
- 130 °C
Procedure
A suspension of 5-bromo-2-hydroxy-3-nitro-pyridine (10 g; ex. Maybridge) in phosphorus oxychloride (10 ml) was heated at 130° C. to give a red solution. The solution was heated at 130° C. for 2.5. The reaction mixture was poured onto iced water and then neutralised by the portionwise addition of solid sodium bicarbonate. The aqueous was extracted twice with ethyl acetate and the combined organics were dried (MgSO4), filtered and evaporated to give the title compound as a yellow solid (10.28 g).
Workup
- customto give a red solution
- temperatureThe solution was heated at 130° C. for 2.5
- extractionThe aqueous was extracted twice with ethyl acetate
- dry with materialthe combined organics were dried (MgSO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-06894082a80c4008a9a4e81b1a32cafc
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589206B2
Reaction notes
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