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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 557618Erstellt: 24. Oktober 2026

1,2-Dibromoethane → 1-(Biphenyl-4-YL)-cyclopropanecarbonitrile

https://huagongshe.com/de/reaction/557618

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt1,2-DibromoethaneHCID 7839—
EduktEthyl AcetateHCID 8857—
EduktPotassium HydroxideHCID 14797—
Edukt4-BiphenylacetonitrileHCID 35856—
KatalysatorTetrabutylammonium BromideHCID 74236—
LösungsmittelWaterHCID 962—
LösungsmittelTolueneHCID 1140—
Produkt1-(Biphenyl-4-YL)-cyclopropanecarbonitrileHCID 6666052899,4%

Reaktionsbedingungen

Temperatur65 °C

Reaktionsschritte

4-phenyl-phenylacetonitrile (VWR scientific, 55.7 g, 289 mmol) was added to a solution of KOH (161.6 g, 2890 mmol) in water (170 mL) and toluene (550 mL) at room temperature. Tetrabutyl ammonium bromide (9.2 g, 29 mmol) followed by 1,2 dibromoethane (64.9 g, 347 mmol) were added and the solution was heated to 65° C. overnight. Reaction complete by TLC (10% EtOAc/hex). The organic layer was extracted 2 times with dilute hydrochloric acid, dried and evaporated to yield 63 g of 1-(biphenyl-4-yl)cyclopropanecarbonitrile.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08058300B2
Quelldatensatzuspto-grants-2011_11
ORD IDord-0b724cd5e16b465b81f0a7b601e04b9c
Quellennotizuspto-grants-2011_11