1,3-Dibromopropane → 1-Phenylcyclobutanecarbonitrile

HRID 388822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 388822
[H-].[Na+].[C:3]1([CH2:9][C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:13][CH2:14][CH2:15]Br.O.C1(C)C=CC=CC=1>CN(C=O)C>[C:3]1([C:9]2([C:10]#[N:11])[CH2:15][CH2:14][CH2:13]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

6

Edukt 4

HCID 80011,3-DibromopropaneHCID 8794PhenylacetonitrileHCID 24758Sodium hydrideHCID 22272177Toluene water

Produkt 1

HCID 844001-PhenylcyclobutanecarbonitrileAusbeute 64,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium hydride (1.54 g, 64.1 mmol) dissolved in DMF (15 ml) and cooled to 0° C. Phenyl acetonitrile (3 g, 25.6 mmol) and 1,3-dibromopropane (5.2 g, 25.6 mmol) were dissolved in DMF (15 ml) and added to above mixture drop-wise at 0° C. This mixture was heated to rt and continued stirring for 2 h. Work up (H2O/Toluene) afforded the title compound (2.61 g) as crude, which was used in the next without further purification.

Aufarbeitung

  1. additionadded to above mixture drop-wise at 0° C
  2. temperatureThis mixture was heated to rt

Quellen und Nachweise

ORD-Eintrag
ord-ab72727df51f4f6ca5969b20ac909818
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377970B2

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