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

HRID 1901131

Reaktionsgleichung

Reaktionsgleichung von HRID 1901131
[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-d58713bc185f48cf969975b9d3796498
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05576338

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