Acetyl bromide → 4-Bromo-6,6'-dimethyl-2,2'-bipyridine

HRID 1586927Notes

Reaction equation

HRID 1586927 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N+]([O-])=O)[CH:5]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=2)[N+:7]=1[O-].[OH-].[Na+].C([Br:24])(=O)C>P(Br)(Br)Br>[Br:24][C:4]1[CH:3]=[C:2]([CH3:1])[N:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 10482Acetyl bromideHCID 14798Sodium HydroxideHCID 110321326,6'-Dimethyl-4-nitro-2,2'-bipyridine-N-oxide

Product 1

HCID 118322434-Bromo-6,6'-dimethyl-2,2'-bipyridine

Reagents, catalysts & solvents 1

HCID 24614Phosphorus tribromideSolvent

Procedure

6,6'-Dimethyl-4-nitro-2,2'-bipyridine-N-oxide (0.50 g, 2.0 mmoles) was dissolved in acetyl bromide (10.0 ml) and phosphorus tribromide (2.5 ml). After refluxing for 1.5 hours the mixture was poured into 100 g ice and the solution was neutralized with 30% sodium hydroxide solution. The mixture was extracted with chloroform, the chloroform phase was dried and evaporated. The product was purified by means of flash chromatography.

Workup

  1. temperatureAfter refluxing for 1.5 hours the mixture
  2. extractionThe mixture was extracted with chloroform
  3. dry with materialthe chloroform phase was dried
  4. customevaporated
  5. customThe product was purified by means of flash chromatography

Sources & evidence

ORD record
ord-1c109e159f09407a99c521bc04376b94
Source dataset
uspto-grants-1993_06
Patent number
US05216134

Reaction notes

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