Ammonium Chloride → Ethanone, 1-(4-chloro-3-fluorophenyl)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-

HRID 2279450Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2279450
[Si:1]([O:8][CH2:9][C:10](N(OC)C)=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([Mg]Br)=[CH:19][C:18]=1[F:25].[NH4+].[Cl-]>C1COCC1>[Si:1]([O:8][CH2:9][C:10]([C:20]1[CH:21]=[CH:22][C:17]([Cl:16])=[C:18]([F:25])[CH:19]=1)=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 116010942-(tert-butyldimethylsilyloxy)-N-methoxy-N-methylacetamideHCID 178505943HCID 178505943, Verbindung

Produkt 1

HCID 68294408Ethanone, 1-(4-chloro-3-fluorophenyl)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-Ausbeute 93,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 60 (15.12 g, 64.79 mmol) and THF (50 mL) cooled to 0° C. was added dropwise (4-chloro-3-fluorophenyl)magnesium bromide (226.8 mL, 113.4 mmol) and the solution was stirred at 0° C. for 2 h. Saturated NH4Cl was added and the reaction was extracted with DCM. The organic layer was separated, dried, filtered and concentrated. The crude product was purified by passage through a SiO2 plug eluting with 5% EtOAc/hexane to afford 18.36 g (93.6%) of 2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethanone (62).

Aufarbeitung

  1. extractionthe reaction was extracted with DCM
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by passage through a SiO2 plug
  7. washeluting with 5% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-d5290904d5624326901fbd297282c949
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133187B2

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