Ethyl Acetate → 5-Bromo-3-(trifluoromethyl)quinoline

HRID 1519824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1519824
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.[Br:15]N1C(=O)CCC1=O.[OH-].[Na+].C(OCC)(=O)C>S(=O)(=O)(O)O.S([O-])([O-])=O.[Na+].[Na+]>[Br:15][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][C:3]([C:2]([F:1])([F:13])[F:14])=[CH:12]2.[Br:15][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[CH:12]=[C:3]([C:2]([F:1])([F:13])[F:14])[CH:4]=[N:5]2

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 120251663-(Trifluoromethyl)quinoline

Produkt 2

HCID 469415118-Bromo-3-(trifluoromethyl)quinolineHCID 687590145-Bromo-3-(trifluoromethyl)quinolineAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1118Sulfuric AcidLösungsmittelHCID 24437Sodium SulfiteLösungsmittel

Versuchsvorschrift

3-(Trifluoromethyl)quinoline (7.00 g, 35.5 mmol) and N-bromosuccinimide (9.00 g, 50.6 mmol) in concentrated sulfuric acid (50 ml) was heated to 50° C. After stirring for 1.5 h, the solution was cooled to ambient temperature, diluted with saturated aq. sodium sulfite, made alkaline with 3 N aq. sodium hydroxide, and extracted with methylene chloride. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was flash chromatographed with 99:1, 49:1, 24:1, and 23:2 hexane:ethyl acetate as the eluant to afford 4.55 g of impure 8-bromo-3-(trifluoromethyl)quinoline and 3.89 g (37% yield) of 5-bromo-3-(trifluoromethyl)quinoline. Method [8] Retention time 6.75 and 7.47 min by HPLC (M+=276 and 278) and (M+=276 and 278).

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customchromatographed with 99:1, 49:1, 24:1, and 23:2 hexane

Quellen und Nachweise

ORD-Eintrag
ord-34a2bfb8ca4a40789ddb9479e78eac90
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073891B2

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