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2,2,2,4'-Tetrafluoroacetophenone → 2,2,2-Trifluoro-1-(4-fluoro-phenyl)-1-[4-(1,1,1,3,3,3-hexamethyl disilazan-2-yl)-3,5-dimethyl-phenyl]-ethanol

HRID 1917052
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1917052
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]([Si:14]([CH3:17])([CH3:16])[CH3:15])[Si:10]([CH3:13])([CH3:12])[CH3:11])=[C:4]([CH3:18])[CH:3]=1.C([Li])CCC.[F:24][C:25]([F:36])([F:35])[C:26]([C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)=[O:27]>O1CCCC1>[F:36][C:25]([F:24])([F:35])[C:26]([C:28]1[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=1)([C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]([Si:14]([CH3:17])([CH3:16])[CH3:15])[Si:10]([CH3:13])([CH3:12])[CH3:11])=[C:4]([CH3:18])[CH:3]=1)[OH:27]
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Komponenten

5

Edukt 3

HCID 695642,2,2,4'-TetrafluoroacetophenoneHCID 594978222-(4-Bromo-2,6-dimethyl-phenyl)-1,1,1,3,3,3-hexamethyl-disilazaneHCID 178418339Butyllithium

Produkt 1

HCID 594978232,2,2-Trifluoro-1-(4-fluoro-phenyl)-1-[4-(1,1,1,3,3,3-hexamethyl disilazan-2-yl)-3,5-dimethyl-phenyl]-ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a solution of 2-(4-bromo-2,6-dimethyl-phenyl)-1,1,1,3,3,3-hexamethyl-disilazane (Example II) (1.72 g, 5.0 mmol) in tetrahydrofuran (12 ml) under a nitrogen atmosphere was slowly added a solution of n-butyl lithium in hexanes (1.6 M) (3.3 ml, 5.28 mmol) at −70° C. The reaction mixture was stirred at −70° C. for 30 minutes before addition of 2,2,2,4′-tetrafluoroacetophenone (commercially available) (1.01 g, 5.25 mmol) at −70° C. The cooling bath was removed after 15 minutes. Once the reaction mixture had reached ambient temperature, it was poured onto water. The mixture was extracted with diethyl ether. The organic phase was washed with water and brine, dried over sodium sulfate, and then concentrated. The title compound was isolated as a yellow oil.

Aufarbeitung

  1. customThe cooling bath was removed after 15 minutes
  2. customhad reached ambient temperature
  3. additionit was poured onto water
  4. extractionThe mixture was extracted with diethyl ether
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fd90c40e3b4d43f995710731cd943f44
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08618173B2

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