Dimethylformamide → 2-(Propan-2-yl)benzaldehyde

HRID 72619

Reaktionsgleichung

Reaktionsgleichung von HRID 72619
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:10])[CH3:9].[Li]CCCC.CN([CH:19]=[O:20])C>C1COCC1.[Cl-].[NH4+]>[CH:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:19]=[O:20])([CH3:10])[CH3:9]

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 23475o-BromocumeneHCID 178418339Butyllithium

Produkt 1

HCID 5905362-(Propan-2-yl)benzaldehydeAusbeute 94,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

To a solution of 2-bromoisopropyl benzene (2.0 g, 10.0 mmole) in dry THF (20 mL), nBuLi (1.6 M in hexane), (6.9 mL, 11.05 mmole) was added at −78° C. and the mixture was stirred at same temperature for one hour. DMF (0.9 g, 12.0 mmole) was added and the mixture was stirred at −78° C. for half an hour then allowed to stir at 0° C. for 15 min. The reaction mixture was diluted with saturated aqueous ammonium chloride (10 mL) and extracted with EtOAc (3×30 mL). The organic layers were combined and washed with brine, dried over sodium sulfate, and concentrated to yield 2-isopropyl benzaldehyde (1.4 g).

Aufarbeitung

  1. stirringthe mixture was stirred at −78° C. for half an hour
  2. stirringto stir at 0° C. for 15 min
  3. extractionextracted with EtOAc (3×30 mL)
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-82f58b64ce604f05bab1eb59545a754a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828951B2

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