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Potassium Carbonate → Tert-butyl-[3-(5-fluoro-2-methoxy-4-nitro-phenoxy)-propoxy]-dimethyl-silane

HRID 1667769
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1667769
[F:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[CH:4][C:5]([O:9][CH3:10])=[C:6]([OH:8])[CH:7]=1.Br[CH2:15][CH2:16][CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O>[C:22]([Si:19]([O:18][CH2:17][CH2:16][CH2:15][O:8][C:6]1[CH:7]=[C:2]([F:1])[C:3]([N+:11]([O-:13])=[O:12])=[CH:4][C:5]=1[O:9][CH3:10])([CH3:20])[CH3:21])([CH3:24])([CH3:25])[CH3:23]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 67426546HCID 67426546, Verbindung

Produkt 1

HCID 67428158Tert-butyl-[3-(5-fluoro-2-methoxy-4-nitro-phenoxy)-propoxy]-dimethyl-silaneAusbeute 69,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 0.350 g (1.87 mmole) of 5-fluoro-2-methoxy-4-nitro-phenol, 0.568 g (2.25 mmole) of (3-bromo-propoxy)-tert-butyl-dimethyl-silane, 1.29 g (9.35 mmole) of potassium carbonate and 5 mL of dimethylformamide was heated at 60 degrees for 3 hours. The mixture was cooled, poured into 50 mL of dilute ammonium chloride solution and extracted three times with 25 mL of ethyl acetate. The combined organic extracts were washed three times with 25 mL of water, once with 25 mL of brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with dichloromethane-hexanes (60:40) to give 0.469 g of tert-butyl-[3-(5-fluoro-2-methoxy-4-nitro-phenoxy)-propoxy]-dimethyl-silane (IV.42) as a white solid.

Aufarbeitung

  1. temperaturewas heated at 60 degrees for 3 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted three times with 25 mL of ethyl acetate
  4. washThe combined organic extracts were washed three times with 25 mL of water
  5. dry with materialonce with 25 mL of brine, dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with dichloromethane-hexanes (60:40)

Quellen und Nachweise

ORD-Eintrag
ord-087fb06fdbae407490f4b9ec4d10671f
Quelldatensatz
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08044213B2

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