Sodium Iodide → Tert-butyl-[2-(2,3-difluoro-4-methyl-5-nitro-phenoxy)-ethoxy]-dimethyl-silane
Reaktionsgleichung
[F:1][C:2]1[C:7]([F:8])=[C:6]([CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[OH:13].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+].Br[CH2:23][CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]>CN1C(=O)CCC1.O>[C:29]([Si:26]([O:25][CH2:24][CH2:23][O:13][C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[C:6]([CH3:9])=[C:7]([F:8])[C:2]=1[F:1])([CH3:28])[CH3:27])([CH3:32])([CH3:31])[CH3:30]Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
To a solution of 2,3-difluoro-4-methyl-5-nitro-phenol (1.02 g, 5.39 mmol) in NMP (10 ml) was added cesium carbonate (2.28 g, 7.01 mmol), sodium iodide (0.807 g, 5.39 mmol) and 2-bromoethoxy tertbutyldimethylsilane (1.5 ml, 7.01 mmol). The mixture was heated at 100° C. for one hour, then cooled to room temperature. Water was added and the mixture was extracted with EtOAc. The combined extracts were washed with water and brine, dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the crude product by flash chromatography (hexanes:EtOAc 9:1) gave 1.16 g (62%) of tert-butyl-[2-(2,3-difluoro-4-methyl-5-nitro-phenoxy)-ethoxy]-dimethyl-silane as a tan solid.
Aufarbeitung
- temperaturecooled to room temperature
- extractionthe mixture was extracted with EtOAc
- washThe combined extracts were washed with water and brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated to dryness under reduced pressure
- customPurification of the crude product by flash chromatography (hexanes:EtOAc 9:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-14eb0a2d2b3646d48bf375058c96034b
- Quelldatensatz
- uspto-grants-2012_10
- Patentnummer
- US08288552B2
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