Benzyl Bromide → 3-Benzyl-1-methyl-4-phenylimidazolium bromide

HRID 874170Notes

Reaction equation

HRID 874170 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]=[CH:3]1.[CH2:13]([Br:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[Br-:20].[CH2:13]([N:4]1[C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[CH:6][N+:2]([CH3:1])=[CH:3]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 27487821-methyl-4-phenyl-1H-imidazole

Product 1

HCID 866551853-Benzyl-1-methyl-4-phenylimidazolium bromideYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a 25 ml one-necked flask, there is dissolved 0.320 g (2.023 mmol) of 1-methyl-4-phenylimidazole, which was obtained according to P. Benjes et al., Heterocycles (1994), 37(2), 735-38, in 10 ml of toluene and then 0.36 ml (3.035 mmol) of benzyl bromide is added. After 5 days of heating under reflux, the reaction medium is concentrated under reduced pressure. The residue is taken up in 50 ml of diisopropyl ether. The precipitate formed is drained, washed twice with 5 ml of diisopropyl ether, and then dried under reduced pressure. 0.500 g (90%) of 3-benzyl-1-methyl-4-phenylimidazolium bromide is thus obtained in the form of a beige-grey solid whose characteristics are the following:

Workup

  1. customwhich was obtained
  2. temperatureAfter 5 days of heating
  3. temperatureunder reflux
  4. concentrationthe reaction medium is concentrated under reduced pressure
  5. customThe precipitate formed
  6. washwashed twice with 5 ml of diisopropyl ether
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-b76324b302074a889d15618937c7aee1
Source dataset
uspto-grants-2015_03
Patent number
US08980875B2

Reaction notes

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