6-Methylquinoline → 6-(Bromomethyl)quinoline

HRID 1442727Notes

Reaction equation

HRID 1442727 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-a514dad896f64a3089b1c2d0ed689028
Source dataset
uspto-grants-2010_02
Patent number
US07659268B2

Reaction notes

Loading…