Phosphorus oxybromide → 2-Bromo-5-methyl-3-nitropyridine

HRID 1363040Notes

Reaction equation

HRID 1363040 reaction equation
P(Br)(Br)([Br:3])=O.O[C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:10]([CH3:16])=[CH:9][N:8]=1>CN(C=O)C>[Br:3][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:10]([CH3:16])=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 178430719HCID 178430719, compound

Product 1

HCID 123624472-Bromo-5-methyl-3-nitropyridineYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

POBr3 (222.8 g, 0.78 mol) was added in portions to 2-hydroxy-5-methyl-3-nitropyridine (100 g, 0.65 mol) in DMF (500 mL) with stirring at 0-10° C. then the reaction mixture was stirred at 80° C. under nitrogen for 12 hours. Reaction mixture was cooled and poured into crushed ice (1 Kg), obtained solid was filtered, washed thoroughly with ice-cold water (2×500 mL), dried in a desiccator under high vacuum for one day to obtain 2-bromo-5-methyl-3-nitropyridine as yellow solid (121 g) in 86% yield. (M+H) Expected: 217; found 216.9.

Workup

  1. stirringthe reaction mixture was stirred at 80° C. under nitrogen for 12 hours
  2. customReaction mixture
  3. temperaturewas cooled
  4. additionpoured
  5. customobtained solid
  6. filtrationwas filtered
  7. washwashed thoroughly with ice-cold water (2×500 mL)
  8. customdried in a desiccator under high vacuum for one day

Sources & evidence

ORD record
ord-c8d239c37ef74ee7b797e1dabac35da4
Source dataset
uspto-grants-2011_02
Patent number
US07884110B2

Reaction notes

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