5-Acetyl-2-bromopyridine → 2-bromo-1-(6-bromopyridin-3-yl)ethanone
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
Product 1
Reagents, catalysts & solvents 1
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)+.