Pyridiniumtribromide → HCID 58497180, compound

HRID 1191089Notes

Reaction equation

HRID 1191089 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:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][N:26]=1)(=[O:24])[CH3:23]>C1COCC1>[Br:1][CH2:23][C:22]([C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][N:26]=1)=[O:24]

Participants

4

Reactant 2

HCID 21124087PyridiniumtribromideHCID 231037476-Acetylnicotinonitrile

Product 1

HCID 58497180HCID 58497180, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add pyridinium tribromide (9.2 g, 28.7 mmol) to a solution of 6-acetyl-nicotinonitrile (4.2 g, 28.7 mmol) in THF (200 mL) at room temperature. Filter off the solids and wash with minimal THF. Recrystallize the solid from EtOAc/hexane to obtain the desired intermediate as a light orange solid (5.2 g, 80%) that was used without further purification. MS (ES−) m/z: 223 (M−H)−.

Workup

  1. filtrationFilter off the solids
  2. washwash with minimal THF
  3. customRecrystallize the solid from EtOAc/hexane

Sources & evidence

ORD record
ord-a2ba5f3be8894b238c00062ffbd9f7b0
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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