8-Methylquinoline → 8-(Bromomethyl)quinoline

HRID 1088783Notes

Reaction equation

HRID 1088783 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:12][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

5

Reactant 2

HCID 119108-MethylquinolineHCID 67184N-bromobutanimide

Product 1

HCID 3469148-(Bromomethyl)quinolineYield 57.7%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

8-Methylquinoline (4.02 g) was dissolved in carbon tetrachloride (40 ml), and N-bromosuccinimide (5.98 g) and benzoyl peroxide (0.15 g) were added to the solution, and the mixture was heated and refluxed for 3 hours. After filtering off the insoluble matter, the filtrate was concentrated. The resultant residue was recrystallized from ligroin to give 8-bromomethylquinoline (3.60 g).

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 3 hours
  3. filtrationAfter filtering off the insoluble matter
  4. concentrationthe filtrate was concentrated
  5. customThe resultant residue was recrystallized from ligroin

Sources & evidence

ORD record
ord-73c260271768461f84e338405dcbac78
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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