Acetic Acid → 3-bromo-2-phenyl-4H-chromen-4-one

HRID 1037266

Reaktionsgleichung

Reaktionsgleichung von HRID 1037266
[C:1]1([C:7]2[O:8][C:9]3[C:14]([C:15](=[O:17])[CH:16]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C.[Br:22]N1C(=O)CCC1=O>O>[Br:22][C:16]1[C:15](=[O:17])[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:8][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 10680FlavoneHCID 67184N-bromobutanimide

Produkt 1

HCID 4662783-bromo-2-phenyl-4H-chromen-4-oneAusbeute 41,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a round-bottom flask was added 2-phenyl-chromen-4-one (0.94 g, 4.23 mmol), acetic acid (40 mL) and N-bromosuccinimide (0.83 g, 4.65 mmol). The reaction mixture was heated to 100° C. using a hot oil bath with a water cooled reflux condenser, while stirring for 1 hour. The reaction mixture was cooled to RT and the solvents were removed in vacuo. The residue was suspended in ethyl acetate, washed with a saturated aqueous sodium hydrogen carbonate solution, dried (MgSO4), filtered, and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (10:1 hexane:EtOAc) to give a white solid (527 mg, 41%). 1H-NMR (400 MHz, CDCl3) δ 8.31 (d, 1H), 7.75 (d, 2H), 7.72 (dd, 1H), 7.45-7.56 (m, 5H).

Aufarbeitung

  1. temperaturecooled
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture was cooled to RT
  4. customthe solvents were removed in vacuo
  5. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was purified by silica gel chromatography (10:1 hexane:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-94e1bf3ef848487a943a2173532ea18a
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546376B2

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