Triethylamine → 2-Bromo-3,4-dimethoxybenzonitrile

HRID 1582382

Reaktionsgleichung

Reaktionsgleichung von HRID 1582382
Cl.NO.C([N:6]([CH2:9][CH3:10])CC)C.[Br:11][C:12]1[C:19]([O:20][CH3:21])=[C:18]([O:22][CH3:23])[CH:17]=[CH:16]C=1C=O.CS(Cl)(=O)=O>C(#N)C>[Br:11][C:12]1[C:19]([O:20][CH3:21])=[C:18]([O:22][CH3:23])[CH:17]=[CH:16][C:10]=1[C:9]#[N:6]

Komponenten

6

Edukt 4

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chlorideHCID 443297Hydroxyamine hydrochlorideHCID 6185382-Bromo-3,4-dimethoxybenzaldehyde

Produkt 1

HCID 227212152-Bromo-3,4-dimethoxybenzonitrileAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

A mixture of hydroxylamine hydrochloride (1.42 g, 20. 4 mmol) and triethylamine (5.7 ml, 40.8 mmol) in acetonitrile (10 ml) was stirred at room temperature for 15 minutes before a solution of 2-bromo-3,4-dimethoxybenzaldehyde (5.0 g, 20.4 mmol) in acetonitrile (40 ml) was added over 40 minutes. The resulting mixture was stirred overnight before a fifth of the resulting solution was charged with methanesulfonyl chloride (0.74 ml, 10 mmol total) and triethylamine (0.6 ml, 4.3 mmol total) portionwise over 6 hours. The mixture was stirred overnight, quenched with water, extracted with ethyl acetate, dried over MgSO4 and concentrated in-vacuo to give 0.90 g of the subtitle product (93%).

Aufarbeitung

  1. additionwas added over 40 minutes
  2. stirringThe mixture was stirred overnight
  3. customquenched with water
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in-vacuo

Quellen und Nachweise

ORD-Eintrag
ord-66f67991ab1245b8a7aca6ef96431ff1
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06734303B2

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