Dimethylformamide → 3-formyl-5-methoxybenzonitrile

HRID 602589Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602589
Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH:5]=[O:6].[CH3:12][N:13](C=O)C>[C-]#N.[C-]#N.[Zn+2]>[CH:5]([C:4]1[CH:3]=[C:2]([CH:9]=[C:8]([O:10][CH3:11])[CH:7]=1)[C:12]#[N:13])=[O:6]

Komponenten

4

Edukt 2

HCID 6228Dimethylformamide2×HCID 106086983-Bromo-5-methoxybenzaldehyde

Produkt 1

HCID 722141823-formyl-5-methoxybenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11186Zinc cyanide (Zn(CN)2)Katalysator

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

step 3—A solution of 3-bromo-5-methoxy-benzaldehyde (1 mmol) in DMF (2 mL) is added to a round bottomed flask containing Zn(CN)2 (0.7 equivalents), Pd(PPh3)4(0) (0.2 equivalents) in DMF (15 mL). The reaction is stirred at 90° C. under an atmosphere of argon for 48 h. The reaction mixture is cooled and evaporated to dryness. The crude residue is dissolved in EtOAc, washed with brine solution, dried (MgSO4) and evaporated. The crude product is purified by SiO2 chromatography to afford 3-formyl-5-methoxy-benzonitrile.

Aufarbeitung

  1. temperatureThe reaction mixture is cooled
  2. customevaporated to dryness
  3. dissolutionThe crude residue is dissolved in EtOAc
  4. washwashed with brine solution
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product is purified by SiO2 chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5828124f870e4f48a26c2bf299046d2d
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906540B2

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