Tert-butyl-[2-(2,3-difluoro-4-methyl-5-nitro-phenoxy)-ethoxy]-dimethyl-silane → 5-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-3,4-difluoro-2-methyl-phenylamine

HRID 2065747Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2065747
[C:1]([Si:5]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[C:16]([N+:18]([O-])=O)[C:15]([CH3:21])=[C:14]([F:22])[C:13]=1[F:23])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([Si:5]([CH3:7])([CH3:6])[O:8][CH2:9][CH2:10][O:11][C:12]1[C:13]([F:23])=[C:14]([F:22])[C:15]([CH3:21])=[C:16]([NH2:18])[CH:17]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 1

HCID 59378019Tert-butyl-[2-(2,3-difluoro-4-methyl-5-nitro-phenoxy)-ethoxy]-dimethyl-silane

Produkt 1

HCID 593779115-[2-(Tert-butyl-dimethyl-silanyloxy)-ethoxy]-3,4-difluoro-2-methyl-phenylamineAusbeute 60,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl-[2-(2,3-difluoro-4-methyl-5-nitro-phenoxy)-ethoxy]-dimethyl-silane (1.16 g, 3.33 mmol) in EtOH (10 ml) was added 10% Pd/C (0.116 g) and the mixture was hydrogenated under balloon pressure for two hours. The mixture was filtered and the filtrate was concentrated to dryness under reduced pressure. Purification of the crude product by flash chromatography (hexanes:EtOAc 7:3) gave 0.638 g of 5-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-3,4-difluoro-2-methyl-phenylamine as a tan solid.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness under reduced pressure
  3. customPurification of the crude product by flash chromatography (hexanes:EtOAc 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-c7936c35252b4ee380b4bc176719677b
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288552B2

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