Dimethylformamide → 3-Bromo-2-chloro-5-nitropyridine

HRID 1976054Notes

Reaction equation

HRID 1976054 reaction equation
[Br:1][C:2]1[C:3](O)=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.CN(C=O)C.P(Cl)(Cl)([Cl:19])=O>C(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]([Cl:19])=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 178526832HCID 178526832, compound

Product 1

HCID 2308893-Bromo-2-chloro-5-nitropyridineYield 95.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Bromo-2-hydroxy-5-nitropyridine (8.5 g, 39 mmol) and N,N′-dimethylformamide (0.5 ml) in chloroform (75 ml) were treated dropwise with phosphorous oxychloride (7.3 ml, 80.2 mmol) and heated at reflux for 24 hrs. The mixture was then cooled and concentrated, before being partitioned between ethyl acetate (80 ml) and sodium hydrogen carbonate solution (50 ml). The organic phase was washed with brine (100 ml), dried Na2SO4) and concentrated to give the product as a yellow solid (8.88 g).

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 hrs
  3. temperatureThe mixture was then cooled
  4. concentrationconcentrated
  5. custombefore being partitioned between ethyl acetate (80 ml) and sodium hydrogen carbonate solution (50 ml)
  6. washThe organic phase was washed with brine (100 ml), dried Na2SO4) and
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fd5190bd481f4938be84188179858aa3
Source dataset
uspto-grants-2001_05
Patent number
US06225320B1

Reaction notes

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