N-bromobutanimide → 1,1-dimethylethyl 6-bromo-7-hydroxy-8-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

HRID 1668585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1668585
[OH:1][C:2]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][C:4]=2[CH:3]=1.C1C(=O)N([Br:30])C(=O)C1>C(Cl)Cl>[Br:30][C:3]1[C:4]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[CH2:7][CH2:6][C:5]=2[CH:18]=[C:19]([N+:20]([O-:22])=[O:21])[C:2]=1[OH:1]

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 589728117-Hydroxy-8-nitro-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid tert-butyl ester

Produkt 1

HCID 591505311,1-dimethylethyl 6-bromo-7-hydroxy-8-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylateAusbeute 80,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Bromination of 1,1-dimethylethyl 7-hydroxy-8-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (71 mg) was performed with NBS (41 mg) in DCM (2.2 ml) and SiO2 (426 mg) at −15° C. under nitrogen. After 15 minutes SiO2 was filtered off and the solvent was evaporated under reduced pressure. The crude was purified on silica gel (ethyl acetate/petroleum ether, 1/9) obtaining the title compound as a yellow solid (72 mg).

Aufarbeitung

  1. filtrationAfter 15 minutes SiO2 was filtered off
  2. customthe solvent was evaporated under reduced pressure
  3. customThe crude was purified on silica gel (ethyl acetate/petroleum ether, 1/9)

Quellen und Nachweise

ORD-Eintrag
ord-f1a4aad038654991961622ddadc81474
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989444B2

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