Phenol → 2-Methyl-4-phenoxy-8-bromo-quinoline

HRID 1700114

Reaktionsgleichung

Reaktionsgleichung von HRID 1700114
[CH3:1][C:2]1[CH:11]=[C:10](Cl)[C:9]2[C:4](=[C:5]([Br:13])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:14]1([OH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[K+]>C(Cl)Cl>[CH3:1][C:2]1[CH:11]=[C:10]([O:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]2[C:4](=[C:5]([Br:13])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Komponenten

5

Edukt 3

HCID 996PhenolHCID 14797Potassium HydroxideHCID 7684838-Bromo-4-chloro-2-methylquinoline

Produkt 1

HCID 183178152-Methyl-4-phenoxy-8-bromo-quinolineAusbeute 84,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Part B: A mixture of 5.0 g (19.5 mmol) of 2-methyl-4-chloro-8-bromo-quinoline, 18.3 g (195 mmol) of phenol and 2.5 g (87%, 39 mmol) of KOH was heated at 120° C. under nitrogen for 30 min. After cooling 500 ml of CH2Cl2 was added and the mixture was extracted with 250 ml of 1N NaOH. After concentration of the organic layer in vacuo the residue was dissolved in ether and again extracted with 50 ml of 1N NaOH and 50 ml of brine. The organic layer was dried over magnesium sulphate and concentrated in vacuo. A total of 5.2 g of 2-methyl-4-phenoxy-8-bromo-quinoline was obtained as a white solid (85% yield).

Aufarbeitung

  1. additionwas added
  2. extractionthe mixture was extracted with 250 ml of 1N NaOH
  3. dissolutionAfter concentration of the organic layer in vacuo the residue was dissolved in ether
  4. extractionagain extracted with 50 ml of 1N NaOH and 50 ml of brine
  5. dry with materialThe organic layer was dried over magnesium sulphate
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-42e6c802722443f5884c5a1eaf0fd463
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06350750B1

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