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

HRID 1191083Notes

Reaction equation

HRID 1191083 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:31][C:28]1[CH:27]=[CH:26][C:25]([C:22](=[O:24])[CH2:23][Br:1])=[CH:30][N:29]=1

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 (7.0 g, 22 mmol) to a solution of 5-acetyl-2-bromo-pyridine (4.0 g, 20 mmol) in THF (100 mL) at room temperature. Stir the mixture for 16 h at room temperature under a nitrogen atmosphere. Quench the mixture with saturated aqueous NaHCO3 (50 mL, pH to 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 (M+H)+.

Workup

  1. customQuench the mixture with saturated aqueous NaHCO3 (50 mL, pH to 7.8)
  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-5461a30b036c40ce8a1172e97ca717ef
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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