1,3-Dibromopropane → 5,6,7,8-Tetrahydro-1-nitro-2-(3-bromopropoxy)naphthalene
Reaktionsgleichung
C(=O)([O-])[O-].[K+].[K+].[Br:7][CH2:8][CH2:9][CH2:10]Br.[OH:12][C:13]1[CH:22]=[CH:21][C:20]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[C:14]=1[N+:23]([O-:25])=[O:24]>CN(C)C=O>[N+:23]([C:14]1[C:15]2[CH2:16][CH2:17][CH2:18][CH2:19][C:20]=2[CH:21]=[CH:22][C:13]=1[O:12][CH2:10][CH2:9][CH2:8][Br:7])([O-:25])=[O:24]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
N,N-dimethylformamide (180 ml), potassium carbonate (37.8 g, 0.273 mol), and 1,3-dibromopropane (93 ml, 0.916 mol) were added to 2-hydroxy-5,6,7,8-tetrahydro-1-nitronaphthalene (17.6 g, 0.091 mol) and the mixture was stirred at 70° C. for 4 hours. The precipitated salts were removed by filtration, and then the solvent was evaporated and the residue was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The residue was purified by silica gel chromatography (Wako Gell C-300: 500 g, eluent: ethyl acetate/hexane=1/20) to give 5,6,7,8-tetrahydro-1-nitro-2-(3-bromopropoxy)naphthalene (19.4 g).
Aufarbeitung
- customThe precipitated salts were removed by filtration
- customthe solvent was evaporated
- extractionthe residue was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated
- customThe residue was purified by silica gel chromatography (Wako Gell C-300: 500 g, eluent: ethyl acetate/hexane=1/20)
Quellen und Nachweise
- ORD-Eintrag
- ord-c4cb0050bb6f4f3f81ba1e388453dfb5
- Quelldatensatz
- uspto-grants-1998_09
- Patentnummer
- US05807860
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