5-Acetyl-2-bromopyridine → 2-bromo-1-(6-bromopyridin-3-yl)ethanone

HRID 1670539Notes

Reaction equation

HRID 1670539 reaction equation
[Br-:1].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[C:22]([C:25]1[CH:26]=[CH:27][C:28]([Br:31])=[N:29][CH:30]=1)(=[O:24])[CH3:23]>C1COCC1>[Br:1][CH2:23][C:22]([C:25]1[CH:30]=[N:29][C:28]([Br:31])=[CH:27][CH:26]=1)=[O:24]

Participants

4

Reactant 2

HCID 156681955-Acetyl-2-bromopyridineHCID 21124087Pyridiniumtribromide

Product 1

HCID 108502672-bromo-1-(6-bromopyridin-3-yl)ethanoneYield 206.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add pyridinium tribromide (7 g, 22 mmol) to a solution of 5-acetyl-2-bromo-pyridine (4 g, 20 mmol) in THF (100 mL) at room temperature. Stir the mixture for 16 h at ambient temperature under a nitrogen atmosphere. Quench the mixture with saturated aqueous NaHCO3 (50 mL, pH at 7.8). Extract the mixture with EtOAc (150 mL). Wash the organic layer with brine (50 mL) and concentrate in vacuo to obtain the desired intermediate as a dark brown oil (11.5 g) that was used without further purification. MS (ES+) m/z: 280.0 (M+H)+.

Workup

  1. customQuench the mixture with saturated aqueous NaHCO3 (50 mL
  2. extractionExtract the mixture with EtOAc (150 mL)
  3. washWash the organic layer with brine (50 mL)
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-324ef88093034357ade38b42b7370446
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

Loading…