Sulfuric Acid → 1-(2-Bromo-4-pyridinyl)cyclopropanecarboxaldehyde

HRID 1423068Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1423068
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2([C:11]#N)[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.[H-].C([Al+]CC(C)C)C(C)C.CC[O:25]C(C)=O.OS(O)(=O)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2([CH:11]=[O:25])[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 21225700DiisobutylaluminumhydrideHCID 71743245HCID 71743245, Verbindung

Produkt 1

HCID 866727561-(2-Bromo-4-pyridinyl)cyclopropanecarboxaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a chilled (−78° C.) solution of 1-(2-bromopyridin-4-yl)-cyclopropanecarbonitrile (1.16 g, 5.2 mmol) in toluene (30 mL) is added a 1 M solution of diisobutylaluminum hydride (DIBAH) (10.4 mL) in toluene. The mixture stirred at −78° C. for 1 hour and is then warmed to room temperature. After 1 hour, EtOAc (30 mL) is added, followed by 1 M aqueous solution of H2SO4 (30 mL). The organic phase is separated and the aqueous layer is extracted with EtOAc (3×50 mL). The combined organic layers are dried over MgSO4, filtered and concentrated to afford crude 1-(2-bromopyridin-4-yl)-cyclopropanecarboxaldehyde which is used without purification. MS m/z 226.5, 228.5

Aufarbeitung

  1. temperatureis then warmed to room temperature
  2. waitAfter 1 hour
  3. customThe organic phase is separated
  4. extractionthe aqueous layer is extracted with EtOAc (3×50 mL)
  5. dry with materialThe combined organic layers are dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6b3987bf804e440ca28073feafebbac7
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927550B2

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