6-Methylquinoline → 6-(Bromomethyl)quinoline

HRID 1008812Notes

Reaction equation

HRID 1008812 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-fd0684e212c44740b31514534aa9a42c
Source dataset
uspto-grants-2011_07
Patent number
US07973038B2

Reaction notes

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