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

HRID 1900141Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1900141
[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)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 50g 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. 11 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-8aa2f8806bed477c81c34741ae555e22
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05574071

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