Sodium methanethiolate → 4-Bromo-5-hydroxy-2,3-dihydro-1H-inden-1-one
Reaktionsgleichung
C[S-].[Na+].[Br:4][C:5]1[C:13]([O:14]C)=[CH:12][CH:11]=[C:10]2[C:6]=1[CH2:7][CH2:8][C:9]2=[O:16]>CN(C)C=O>[Br:4][C:5]1[C:13]([OH:14])=[CH:12][CH:11]=[C:10]2[C:6]=1[CH2:7][CH2:8][C:9]2=[O:16]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 130 °C
Versuchsvorschrift
Sodium methanethiolate (2.00 g) is added to a microwave vial charged with a stir bar, 4-bromo-5-methoxy-indan-1-one (1.58 g), and N,N-dimethylformamide (10 mL). The vial is sealed and the mixture is heated to 130° C. and stirred at this temperature for 2 h. After cooling to room temperature, the mixture is partitioned between ethyl acetate and 1 N aqueous HCl solution. The aqueous phase is separated and extracted with ethyl acetate. The combined organic phases are washed with brine and dried (MgSO4). The solvents are evaporated and the residue is triturated with diethylether. The precipitate is filtered off and dried in vacuo to give the title compound. LC (method 1): tR=0.84 min; Mass spectrum (ESI+): m/z=227/229 (Br) [M+H]+.
Aufarbeitung
- additionvial charged with a stir bar
- customThe vial is sealed
- temperatureAfter cooling to room temperature
- customthe mixture is partitioned between ethyl acetate and 1 N aqueous HCl solution
- customThe aqueous phase is separated
- extractionextracted with ethyl acetate
- washThe combined organic phases are washed with brine
- dry with materialdried (MgSO4)
- customThe solvents are evaporated
- customthe residue is triturated with diethylether
- filtrationThe precipitate is filtered off
- customdried in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-96d4b3908c694c299770ada0b7e5f536
- Quelldatensatz
- uspto-grants-2014_08
- Patentnummer
- US08809376B2
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