N-bromobutanimide → 1-Acetyl-8-bromo-7-hydroxy-2,3,4,5-tetrahydro-1H-benzazepine

HRID 1741045Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1741045
[C:1]([N:4]1[C:10]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:9]=2[CH2:8][CH2:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Br:16]N1C(=O)CCC1=O>CC(O)=O.C(OCC)(=O)C>[C:1]([N:4]1[C:10]2[CH:11]=[C:12]([Br:16])[C:13]([OH:15])=[CH:14][C:9]=2[CH2:8][CH2:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 218338251-Acetyl-7-hydroxy-2,3,4,5-tetrahydro-1H-benzazepine

Produkt 1

HCID 218338021-Acetyl-8-bromo-7-hydroxy-2,3,4,5-tetrahydro-1H-benzazepineAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1-Acetyl-7-hydroxy-2,3,4,5-tetrahydro-1H-benzazepine (D24, 2.81 g, 14 mmol) was stirred in glacial AcOH (50 ml) as N-bromosuccinimide (2.69 g, 15 mmol) was added portionwise over 20 min. The mixture was stirred for 30 min, diluted with ethyl acetate (500 ml), washed with water, K2CO3 solution and brine, dried (Na2SO4) and evaporated to give a tan solid, shown by NMR and TLC to be a mixture of dibromo and mono-bromo isomers. Chromatography on silica, eluting with 0-25% ethyl acetate/dichloromethane, yielded pure title compound (1.22 g, 31%) as a cream solid.

Aufarbeitung

  1. additionwas added portionwise over 20 min
  2. washwashed with water, K2CO3 solution and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customto give a tan solid
  6. additiona mixture of dibromo and mono-bromo isomers
  7. washChromatography on silica, eluting with 0-25% ethyl acetate/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-7346bbfc15064b649313c71b761e3bb1
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05972951

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