8-Methylquinoline → 5-Bromo-8-methylquinoline

HRID 43194

Reaktionsgleichung

Reaktionsgleichung von HRID 43194
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

Komponenten

5

Edukt 3

HCID 119108-MethylquinolineHCID 14798Sodium HydroxideHCID 67184N-bromobutanimide

Produkt 1

HCID 47150225-Bromo-8-methylquinolineAusbeute 97,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-67903072b86b4e06a90817a7d602ffbc
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536175B2

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