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Dimethylformamide → HCID 57736547, Verbindung

HRID 1641681
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1641681
CCCCCC.C([Li])CCC.Br[C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([CH:20]([C:29]2[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=2[F:36])[S:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[CH:15][N:14]=1.CN(C)[CH:39]=[O:40]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[F:36][C:30]1[CH:31]=[CH:32][C:33]([F:35])=[CH:34][C:29]=1[CH:20]([S:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)[C:16]1[C:17]([CH3:19])=[CH:18][C:13]([CH:39]=[O:40])=[N:14][CH:15]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 57736453HCID 57736453, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 57736547HCID 57736547, VerbindungAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962
Water
Lösungsmittel
HCID 1140TolueneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In an argon atmosphere, a hexane solution of n-butyllithium M, 22.3 ml, 34.4 mmol) was added to a solution of 2-bromo-5-[(2,5-difluorophenyl)[(4-fluorophenyl)thio]methyl]-4-methylpyridine (8.10 g, 19.1 mmol) in toluene (200 ml) at −78° C. The reaction mixture was stirred for 30 minutes, and then N,N-dimethylformamide (1.63 ml, 21.0 mmol) was added at the same temperature. The reaction mixture was stirred for 30 minutes, then water was added at the same temperature, and the mixture was allowed to warm to room temperature. Ethyl acetate was added to the reaction mixture, and the resulting mixture was washed with saturated aqueous ammonium chloride, and then with saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was subjected to flash silica gel chromatography. The fraction obtained from an elution with hexane:ethyl acetate=10:1 was concentrated under reduced pressure, and the resulting residue was washed with a mixed solvent of diethyl ether and hexane and then collected by filtration, thus to obtain the title compound (4.27 g, 11.4 mmol, 60%) as a white solid.

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 30 minutes
  2. washthe resulting mixture was washed with saturated aqueous ammonium chloride
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe fraction obtained from an elution with hexane
  7. concentrationethyl acetate=10:1 was concentrated under reduced pressure
  8. washthe resulting residue was washed with a mixed solvent of diethyl ether and hexane
  9. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-d4ac3fce63454535a5a20e8335876350
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08114886B2

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