Benzyl Bromide → 1-Benzyl-4-methylpyridin-1-ium bromide

HRID 1188757Notes

Reaction equation

HRID 1188757 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1.[CH2:8]([Br:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[Br-:15].[CH2:8]([N+:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 79634-Methylpyridine

Product 1

HCID 152645651-Benzyl-4-methylpyridin-1-ium bromideYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-picoline (9.3 g, 0.1 mol) in toluene (200 mL), benzyl bromide (34.2 g, 0.2 mol) was added dropwise at room temperature. After the addition, the mixture was heated to reflux for 5 hrs. The mixture was cooled to room temperature. The precipitate formed was collected by filtration, washed with toluene and dried under vacuum to give Compound 1 as white solid (21.4 g, 81%). It was used without further purification. The structure of Compound 1 is given below:

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 5 hrs
  4. customThe precipitate formed
  5. filtrationwas collected by filtration
  6. washwashed with toluene
  7. customdried under vacuum

Sources & evidence

ORD record
ord-87ea7f931bf0480dadf3dbdeb2c3a7e6
Source dataset
uspto-grants-2014_03
Patent number
US08674102B2

Reaction notes

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