Methanol → 8-Hydroxy-2-methyl-4-(trifluoromethyl)quinoline

HRID 1420633Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1420633
C[O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([CH3:13])[CH:9]=[C:8]2[C:14]([F:17])([F:16])[F:15].B(Br)(Br)Br.CO.C(=O)(O)[O-].[Na+]>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([CH3:13])[CH:9]=[C:8]2[C:14]([F:17])([F:15])[F:16]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 187822278-Methoxy-2-methyl-4-trifluoromethylquinoline

Produkt 1

HCID 187822758-Hydroxy-2-methyl-4-(trifluoromethyl)quinolineAusbeute 79,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

A solution of 11 g (45.6.10-3 mol) of 8-methoxy-2-methyl-4-trifluoromethylquinoline in 360 ml of dichloromethane is cooled to -60° C. and 228 ml of a 1 M solution of boron tribromide in dichloromethane are added dropwise. The reaction medium is subsequently stirred for 1 hour at room temperature, 250 ml of methanol are then added slowly and stirring is continued for 2 hours. 250 ml of dichloromethane are added and sodium bicarbonate solution is added to render the medium alkaline. The organic phase is separated off, washed with water, dried over sodium sulfate and concentrated under reduced pressure to give 8.25 g of the expected product in the form of brown crystals (yield=79.5%).

Aufarbeitung

  1. stirringstirring
  2. waitis continued for 2 hours
  3. customThe organic phase is separated off
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5bf05cf090114f1cbcd0596553a324db
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06071917

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