Potassium Carbonate → 2-Bromo-5-cyclopropoxybenzonitrile

HRID 1754060Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1754060
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[C:4]#[N:5].C([O-])([O-])=O.[K+].[K+].[CH:17]1(Br)[CH2:19][CH2:18]1>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH:17]2[CH2:19][CH2:18]2)=[CH:6][C:3]=1[C:4]#[N:5]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 78037BromocyclopropaneHCID 153231112-Bromo-5-hydroxybenzonitrile

Produkt 1

HCID 900921522-Bromo-5-cyclopropoxybenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a stirred mixture of 2.50 g (13 mmol) 2-bromo-5-hydroxy-benzonitrile in 100 mL DMF are added 5.23 g (38 mmol) K2CO3 and 3.05 g (25 mmol) cyclopropylbromide. The reaction mixture is stirred for 16 h at 120° C. Afterwards the reaction is quenched by the addition of ice water and extracted with EtOAc. The org. layers are combined, washed with sat. aq. NaCl solution, dried over Na2SO4, filtered and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, PE/EtOAc).

Aufarbeitung

  1. customAfterwards the reaction is quenched by the addition of ice water
  2. extractionextracted with EtOAc
  3. washwashed with sat. aq. NaCl solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo
  7. customThe crude product is purified by column chromatography (silica gel, PE/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-dcb86598e3fa4cc6b8d7b0b568b329bd
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09169205B2

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