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

HRID 1911859Notes

Reaction equation

HRID 1911859 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-5d8da25177304d76a6410e7b4fc4bd8b
Source dataset
uspto-grants-2013_12
Patent number
US08604204B2

Reaction notes

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