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

HRID 1271207Notes

Reaction equation

HRID 1271207 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.P(Cl)(Cl)([Cl:14])=O.O>CN(C=O)C>[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

5

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 178418997HCID 178418997, compound

Product 1

HCID 70194125-Bromo-2-chloro-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (40 mL) was stirred 5-bromo-3-nitro-2-pyridinol (8.76 g, 40 mmol) and the solution treated dropwise with phosphorus oxychloride (28 mL). The solution warmed to 80° for 5 hours. The mixture was cooled to room temperature and carefully poured into a mixture of ice and water (400 mL). This mixture was stirred overnight to precipitate. The solid was collected by filtration, washed with water (2×100 mL) and dried at 65° C. on the high vacuum line for 3 hours to give the title compound. MS: M+−1=237.9 Da.

Workup

  1. temperatureThe solution warmed to 80° for 5 hours
  2. customto precipitate
  3. filtrationThe solid was collected by filtration
  4. washwashed with water (2×100 mL)
  5. customdried at 65° C. on the high vacuum line for 3 hours

Sources & evidence

ORD record
ord-b566bcb3b0e445c3a6ec95f54950524a
Source dataset
uspto-grants-2007_04
Patent number
US07205295B2

Reaction notes

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