Benzyl Bromide → 1-Benzyl-4-methyl-2-formyl-pyridinium bromide

HRID 742470Notes

Reaction equation

HRID 742470 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]=[O:9])[CH:3]=1.[CH2:10]([Br:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>S1(CCCC1)(=O)=O.O>[Br-:17].[CH2:10]([N+:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]=1[CH:8]=[O:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 100118944-Methylpyridine-2-carbaldehyde

Product 1

HCID 190474501-Benzyl-4-methyl-2-formyl-pyridinium bromide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31347SulfolaneSolvent

Procedure

A mixture of 1 g (8.26 mmol) of 4-methylpyridine-2-carboxaldehyde, and 1.41 g (8.3 mmol) of benzyl bromide in 10 mL of sulfolane was stirred and heated on a steam-bath overnight. The resulting mixture was triturated (repeatedly) with ethyl acetate and the solvent was decanted to isolate a dark gum. This residue was dissolved in water, and washed with ether, and the aqueous solution was concentrated in vacuo to afford 1-benzyl-4-methyl-2-formyl-pyridinium bromide, which was used without additional purification.

Workup

  1. temperatureheated on a steam-bath overnight
  2. customThe resulting mixture was triturated (repeatedly) with ethyl acetate
  3. customthe solvent was decanted
  4. customto isolate a dark gum
  5. washwashed with ether
  6. concentrationthe aqueous solution was concentrated in vacuo

Sources & evidence

ORD record
ord-6d78942019454d2b9e9af1b9e663bec1
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

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