Phosphorus pentabromide → 6-Bromonicotinic acid

HRID 1763487Notes

Reaction equation

HRID 1763487 reaction equation
P(Br)(Br)(Br)(Br)[Br:2].O[C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][N:9]=1>O>[Br:2][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 62678Phosphorus pentabromideHCID 178418479HCID 178418479, compound

Product 1

HCID 2389326-Bromonicotinic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phosphorus pentabromide (18 g.) was added carefully to 6-hydroxynicotinic acid (4.17 g) and the resulting mixture was heated with stirring for about 1/4 hour at 70°-80° and then 1 hour at 120°. During the heating, the resulting dark red liquid solidified to a yellow mass. After cooling, the mass was added to iced water, and the resulting white precipitate of 6-bromonicotinic acid was filtered off, washed with water, and recrystallized from aqueous ethanol (yield 4g, m.p. 190°-195°). The compound was used directly in the next stage.

Workup

  1. temperaturethe resulting mixture was heated
  2. custom1 hour
  3. customat 120°
  4. temperatureAfter cooling
  5. filtrationthe resulting white precipitate of 6-bromonicotinic acid was filtered off
  6. washwashed with water
  7. customrecrystallized from aqueous ethanol (yield 4g, m.p. 190°-195°)

Sources & evidence

ORD record
ord-1560ed4f1fb8473c9d054ec3d949cc27
Source dataset
uspto-grants-1978_09
Patent number
US04112102

Reaction notes

Loading…