Phosphorus tribromide → Ethyl 5,6-dibromopyridine-3-carboxylate

HRID 1619129Notes

Reaction equation

HRID 1619129 reaction equation
[Br:1][C:2]1[C:3](O)=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Br:14]P(Br)Br>O>[Br:1][C:2]1[C:3]([Br:14])=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 178469843HCID 178469843, compound

Product 1

HCID 46311326Ethyl 5,6-dibromopyridine-3-carboxylateYield 86.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of ethyl 5-bromo-6-hydroxynicotinate (preparation 47a, 6.35 g, 25.8 mmol), tribromophosphine (2.50 mL, 26 mmol) and phosphorus oxytribromide (7.50 g, 26.2 mmol) was stirred at 120° C. After 3 hours, the mixture was cooled, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and evaporated to yield the title compound (6.88 g, 86%) as a white solid.

Workup

  1. temperaturethe mixture was cooled
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-268c56092cf34e749da9dba46504d315
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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