Tribromoacetaldehyde → 2-(Bromomethyl)-6-methoxyquinoline

HRID 1648106

Reaktionsgleichung

Reaktionsgleichung von HRID 1648106
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([CH3:13])[CH:7]=[CH:6]2.[Br:14]C(Br)(Br)C=O.C(OCC)(=O)C>N1C=CC=CC=1.CN(C)C=O>[Br:14][CH2:13][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=1

Komponenten

6

Edukt 3

HCID 8256TribromoacetaldehydeHCID 8857Ethyl AcetateHCID 706486-Methoxyquinaldine

Produkt 1

HCID 216180432-(Bromomethyl)-6-methoxyquinolineAusbeute 30,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineKatalysatorHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 10 g (57.7 mmol) of 6-methoxy-2-methylquinoline and 30 drops of pyridine in 40 mL of N,N-dimethylformamide was stirred at 60° C. while a solution of 16.21 g (57.7 mmol) of tribromoacetaldehyde in 20 mL of N,N-dimethylformamide was added over 15 min. The reaction mixture was stirred for another 2 hr and then cooled and poured onto 600 mL of ice-water. Work-up with ethyl acetate was carried out in the usual manner. The crude product was purified by flash chromatography on 800 g of silica gel, eluting with hexane-ethyl acetate (4:1) afforded 4.45 g (30.6%) of the title compound as a violet solid. An analytical sample was obtained by recrystallization from ethanol to give colorless crystals, mp 103° C.

Aufarbeitung

  1. additionwas added over 15 min
  2. temperaturecooled
  3. customThe crude product was purified by flash chromatography on 800 g of silica gel
  4. washeluting with hexane-ethyl acetate (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-05f640d1166041ebbf0d4aa9e957cf61
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05434186

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