Dimethylformamide → 5-(1-Fluorocyclopropyl)-2-methoxybenzaldehyde

HRID 406398Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 406398
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([C:13]2([F:16])[CH2:15][CH2:14]2)[CH:10]=[CH:9][C:8]=1[O:17][CH3:18].CN([CH:22]=[O:23])C.C(=O)(O)[O-].[Na+]>C1COCC1>[F:16][C:13]1([C:11]2[CH:10]=[CH:9][C:8]([O:17][CH3:18])=[C:7]([CH:12]=2)[CH:22]=[O:23])[CH2:15][CH2:14]1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 666334672-Bromo-4-(1-fluorocyclopropyl)-1-methoxybenzeneHCID 178418339Butyllithium

Produkt 1

HCID 866626555-(1-Fluorocyclopropyl)-2-methoxybenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

n-Butyllithium (2.7M solution in hexane, 3.42 ml) was added at −78° C. to a solution of 2-bromo-4-(1-fluorocyclopropyl)-1-methoxybenzene (1.88 g) in THF (62 ml), followed by addition of a solution of DMF (650 μl) in THF. After the reaction mixture was stirred at −78° C. for 30 minutes, a saturated aqueous solution of sodium bicarbonate was added to the reaction mixture and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (1.00 g).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4375d25adb354f42be72c9add84c9f60
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754100B2

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