Sodium Hydroxide → 4-(3-Fluoro-4-hydroxybenzoyl)benzonitrile

HRID 1683447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1683447
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[O:18]C)[C:5]([C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1)=[O:6].B(Br)(Br)Br.[OH-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[OH:18])[C:5]([C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1)=[O:6]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 19043702HCID 19043702, Verbindung

Produkt 1

HCID 190437654-(3-Fluoro-4-hydroxybenzoyl)benzonitrileAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 50 g of 4-(3-fluoro-4-methoxy-benzoyl)benzonitrile in 550 ml of methylene chloride is treated with 70 ml of BBr3 at 5° C. and stirred at room temperature. 1 l of 1M NaOH is added dropwise while cooling with ice. Then, the mixture is extracted with saturated aqueous NH4Cl solution and methylene chloride. The organic phase is washed with water and dried. After recrystallization from ether, there are obtained 34 g of 4-(3-fluoro-4-hydroxy-benzoyl)-benzonitrile, m.p. 168.5°-169.5° C.

Aufarbeitung

  1. temperaturewhile cooling with ice
  2. extractionThen, the mixture is extracted with saturated aqueous NH4Cl solution and methylene chloride
  3. washThe organic phase is washed with water
  4. customdried
  5. customAfter recrystallization from ether, there

Quellen und Nachweise

ORD-Eintrag
ord-3ede8702af6345c392830e26176ca46a
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05637771

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