N-bromobutanimide → HCID 23157338, Verbindung

HRID 2110860Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2110860
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:8]([O:10][CH3:11])=[O:9])([CH3:3])[CH3:2].[Br:16]N1C(=O)CCC1=O>C(OCC)(=O)C.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:16][CH2:15][C:14]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[O:4][CH:1]([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 23157412Methyl 3-isopropoxy-4-methylbenzoate

Produkt 1

HCID 23157338HCID 23157338, VerbindungAusbeute 64,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6547AzobisisobutyronitrileKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of methyl 3-isopropoxy-4-methylbenzoate (1.0 g, 4.8 mmol) in ethyl acetate (20 mL) were added N-bromosuccinimide (0.92 g, 5.19 mmol) and 2,2′-azobis(isobutyronitrile) (3 mg), and the mixture was heated under reflux for 6 hr. The reaction mixture was cooled, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=4/1) to give the title compound (0.89 g, yield 64%) as a colorless oil. MS (ESI+): 287 (M+H), 289.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hr
  3. temperatureThe reaction mixture was cooled
  4. washwashed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-8d3f1d5bad4d4079bd133a38260a098a
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517910B2

Notizen zur Reaktion

Wird geladen…