Acetic Acid → N-(6-Bromo-1-oxo-2,3-dihydro-1H-inden-5-yl)acetamide
Reaktionsgleichung
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[Br:14])[CH2:10][CH2:9][CH2:8]2)(=[O:3])[CH3:2].C(O)(=[O:17])C>[O-2].[O-2].[O-2].[Cr+6]>[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[Br:14])[C:10](=[O:17])[CH2:9][CH2:8]2)(=[O:3])[CH3:2]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of 5-acetylamino-6-bromoindane (43.0 g, 0.17 mol) in glacial acetic acid (400 mL) at 50°-55° C. was added dropwise a solution of chromium trioxide (70.0 g, 0,7 mol) in 50% aqueous acetic acid (400 mL) over a period of 30 min. After further stirring for 15 min, the mixture was cooled to 0° C. and quenched with 2-propanol (100 mL). Solvent was removed in vacuo. The residue was diluted with water (1 L) and extracted with ethyl acetate (2×500 mL). The combined ethyl acetate layer was washed with 0.5M aqueous NaOH (1 L), brine, dried over anhydrous MgSO4 and concentrated to give 36 g (80%) of the title compound as a light brown solid which was contaminated with about 10% of 5-bromo-6-acetylamino- 1-indanone. 1H NMR (CDCl3): δ8.60 (1H, s), 7.98 (1H, s), 7.90 (1H, s), 3.10 (2H, t), 2.70 (2H, t), 2.30 (3H, s).
Aufarbeitung
- customquenched with 2-propanol (100 mL)
- customSolvent was removed in vacuo
- additionThe residue was diluted with water (1 L)
- extractionextracted with ethyl acetate (2×500 mL)
- washThe combined ethyl acetate layer was washed with 0.5M aqueous NaOH (1 L), brine
- dry with materialdried over anhydrous MgSO4
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-983fb8ebafa34951baa1dfec606bd1ba
- Quelldatensatz
- uspto-grants-1997_02
- Patentnummer
- US05604260
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