Hydrogen Bromide → 7-bromo-4-(bromoacetyl)-2H-chromen-2-one

HRID 260444

Reaktionsgleichung

Reaktionsgleichung von HRID 260444
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13]([O:15]CC)=[CH2:14])=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.C1C(=O)N([Br:25])C(=O)C1.Br.OS([O-])=O.[Na+]>CC#N.O.C(OCC)(=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13](=[O:14])[CH2:15][Br:25])=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 260Hydrogen BromideHCID 67184N-bromobutanimideHCID 233702047-bromo-4-(1-ethoxyvinyl)-2H-chromen-2-oneHCID 23665763Sodium Bisulfite

Produkt 1

HCID 233702397-bromo-4-(bromoacetyl)-2H-chromen-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Versuchsvorschrift

To a solution of vinyl ether from Step 1 (1.02 g) in CH3CN:H2O 4:1 (25 mL) were successively added NBS (0.82 g) and concentrated HBr (20 μL). After being stirred at r.t. for 4 h, the reaction mixture was treated with 5% aqueous NaHSO3 (1 mL). Ethyl acetate was then added and the organic phase was washed with saturated aqueous NaHCO3, H2O and brine, dried (MgSO4) and evaporated. Flash chromatography of the residue (silica gel; hexane/EtOAc (85:15)) afforded the title compound as a white solid.

Aufarbeitung

  1. washthe organic phase was washed with saturated aqueous NaHCO3, H2O and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ddc0010a3592462f9aa6070e03e8d4a3
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05527827

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