4-Bromophenol → 2-(4-Bromophenoxy)benzonitrile

HRID 51485

Reaktionsgleichung

Reaktionsgleichung von HRID 51485
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[C:4]#[N:5])=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 678552-Fluorobenzonitrile

Produkt 1

HCID 227364352-(4-Bromophenoxy)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 2-fluorobenzonitrile (28.8 g), 4-bromophenol (36.9 g), potassium carbonate (58.9 g) and dimethylformamide (30 ml) was heated with stirring under nitrogen at 120° C. for 5 hours. The mixture was allowed to stand overnight at ambient temperature and then partitioned between ethyl acetate and water. The organic layer was separated, washed, dried and evaporated to give an oil which solidified on standing. The solid was triturated with petroleum ether b.p. 40-60° C. and filtered to give 2-(4-bromophenoxy)benzonitrile.

Aufarbeitung

  1. temperaturewas heated
  2. waitto stand overnight at ambient temperature
  3. custompartitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed
  6. customdried
  7. customevaporated
  8. customto give an oil which
  9. customThe solid was triturated with petroleum ether b.p. 40-60° C.
  10. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-55b7fb0c0aa44265ba7561577d290abe
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713474B2

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