Phosphorus oxychloride → 5-Bromo-2-chloro-3-nitropyridine

HRID 1817907

Reaction equation

HRID 1817907 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](=O)[NH:6][CH:7]=1.P(Cl)(Cl)([Cl:14])=O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([Cl:14])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 851475-Bromo-3-nitro-2-pyridone

Product 1

HCID 70194125-Bromo-2-chloro-3-nitropyridineYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-bromo-3-nitropyridin-2(1H)-one (Step A, 2.5 g, 10.4 mmol), phosphoryl chloride (25 mL) and N,N-dimethylformamide (2.5 mL) was stirred under reflux for 3 h. After removal of solvent, the residue was dissolved in water (20 mL) and diethylether (20 mL) at 0° C. and the solution was separated. The organic layer was washed with saturated sodium hydrogen carbonate, dried over sodium sulfate and concentrated to afford the title compound (2.5 g, 89%) as a pale yellow solid.

Workup

  1. temperatureunder reflux for 3 h
  2. customAfter removal of solvent
  3. dissolutionthe residue was dissolved in water (20 mL)
  4. customdiethylether (20 mL) at 0° C. and the solution was separated
  5. washThe organic layer was washed with saturated sodium hydrogen carbonate
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-676b09dbcdbc4ceeb8a783fc912f8319
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Linked notes

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