Phosphorus oxybromide → 2-Bromo-4-methyl-5-nitropyridine

HRID 398335

Reaction equation

HRID 398335 reaction equation
P(Br)(Br)([Br:3])=O.O[C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][N:8]=1>ClCCCl>[Br:3][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 178429283HCID 178429283, compound

Product 1

HCID 3458732-Bromo-4-methyl-5-nitropyridine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A solution of phosphorus oxybromide (14.4 g, 50 mmol) in 1,2-dichloroethane (50 mL) was added to a stirred suspension of 2-hydroxy-4-methyl-5-nitropyridine (5 g, 32.4 mmol) in 1,2-dichloroethane (50 mL) and the resulting mixture was heated to reflux. After 4 h, the reaction was cooled and quenched with water. The organic layer was dried (Na2SO4), filtered through a pad of silica eluting with chloroform and evaporated in vacuo to give the title compound as a yellow solid:

Workup

  1. temperaturethe resulting mixture was heated to reflux
  2. temperaturethe reaction was cooled
  3. customquenched with water
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered through a pad of silica eluting with chloroform
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-ba4bff50ea604b46a181d9b969880c04
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Linked notes

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