6-Methylquinoline → 6-(Bromomethyl)quinoline

HRID 1879881Notes

Reaction equation

HRID 1879881 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.C1C(=O)N([Br:19])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 70596-MethylquinolineHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimide

Product 1

HCID 2243966-(Bromomethyl)quinolineYield 54%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 6-methylquinoline (2.15 g, 15.0 mmol) in CCl4 (30 mL) was added NBS (2.92 g, 16.5 mmol) and benzoyl peroxide (BP, 0.36 g, 1.5 mmol) at room temperature. The mixture was heated at reflux for 2 hours. After cooling, the mixture was evaporated under vacuum to give a yellow solid, which was extracted with Petroleum Ether (30 mL×5). The extracts were concentrated under vacuum to give crude 6-bromomethylquinoline (1.8 g), which was used directly in the next step.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperatureAfter cooling
  4. customthe mixture was evaporated under vacuum
  5. customto give a yellow solid, which
  6. extractionwas extracted with Petroleum Ether (30 mL×5)
  7. concentrationThe extracts were concentrated under vacuum

Sources & evidence

ORD record
ord-b17bdc2530604391aa15e1198ff38b3f
Source dataset
uspto-grants-2012_11
Patent number
US08318733B2

Reaction notes

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