8-Methylquinoline → 5-Bromo-8-methylquinoline

HRID 2409757Notes

Reaction equation

HRID 2409757 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[CH:15]2.[OH-].[Na+]>OS(O)(=O)=O>[Br:8][C:13]1[CH:12]=[CH:11][C:10]([CH3:9])=[C:19]2[C:14]=1[CH:15]=[CH:16][CH:17]=[N:18]2

Participants

5

Reactant 3

HCID 119108-MethylquinolineHCID 14798Sodium HydroxideHCID 67184N-bromobutanimide

Product 1

HCID 47150225-Bromo-8-methylquinolineYield 97.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
5 °C

Procedure

NBS (13.7 g, 76.9 mmol, 1.1 equiv) was added portionwise to a cold (5° C.) solution of 8-methyl-quinoline (10 g, 69.9 mmol) in concentrated H2SO4 (150 mL). The reaction mixture was stirred for 18 h at 5° C., diluted in ice (300 mL) and basified by addition of an aqueous solution of NaOH (10% wt). The resulting white solid was collected by vacuum filtration, rinsed with water, and dissolved in DCM. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated to afford 15.2 g of the title compound as a beige solid: ESI-MS: 221.9/223.9 [M+H]+; tR=3.59 min (System 1).

Workup

  1. filtrationThe resulting white solid was collected by vacuum filtration
  2. washrinsed with water
  3. dissolutiondissolved in DCM
  4. washThe organic phase was washed with H2O and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ec69696c8c944b73b37973870d981ad0
Source dataset
uspto-grants-2014_08
Patent number
US08815901B2

Reaction notes

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