Phenacyl bromide → 2-methyl-1-(2-oxo-2-phenylethyl)pyridinium bromide

HRID 450026Notes

Reaction equation

HRID 450026 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:7].[Br:8][CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11]>CO>[Br-:8].[CH3:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N+:1]=1[CH2:9][C:10](=[O:11])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 79752-Methylpyridine

Product 1

HCID 123168242-methyl-1-(2-oxo-2-phenylethyl)pyridinium bromideYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Picoline (10.0 g, 0.1 mol) was added to a solution of alpha-bromoacetophenone (21.4 g, 0.1 mol) in methanol (150 ml). The solution was heated to reflux for 1 hr. The solvent was evaporated under vacuum to yield a solid, which was recrystallised from ethyl acetate/methanol. The resulting white solid was dried under vacuum to give 2-methyl-1-(2-oxo-2-phenyl-ethyl)-pyridinium bromide (18.0 g, 86%).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 1 hr
  3. customThe solvent was evaporated under vacuum
  4. customto yield a solid, which
  5. customwas recrystallised from ethyl acetate/methanol
  6. customThe resulting white solid was dried under vacuum

Sources & evidence

ORD record
ord-c636008d933f48098ac8684b75598c11
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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