Ammonia → 2-Bromo-6-(4-methylphenyl)pyrazine

HRID 1269635Notes

Reaction equation

HRID 1269635 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:3]=1.P(Br)(Br)[Br:16].N>O>[Br:16][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24614Phosphorus tribromideHCID 184483262-Chloro-6-(4-methylphenyl)pyrazine

Product 1

HCID 184483232-Bromo-6-(4-methylphenyl)pyrazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a flask containing 2-chloro-6-(4-methylphenyl)pyrazine (2.5 g, 12.3 mmol), was added phosphorus tribromide (20 mL) and the mixture heated at reflux for 6 h under nitrogen. The reaction mixture was cooled to room temperature prior to pouring carefully into iced water (600 mL). The resulting solution was adjusted to pH 6–7 using aqueous ammonia and extracted with Et2O (2×250 mL). The organic solution was dried (MgSO4) and the solvent removed in vacuo to afford the title compound as a white solid (2.32 g).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 6 h under nitrogen
  3. extractionextracted with Et2O (2×250 mL)
  4. dry with materialThe organic solution was dried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-27f4149e1e044c8ebf87231a73f422a9
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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