1,3-Dibromopropane → 1-(4-Bromophenyl)cyclobutanecarbonitrile

HRID 603143Notizen

Reaktionsgleichung

[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1.Br[CH2:14][CH2:15][CH2:16]Br>CS(C)=O.O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:11]#[N:12])[CH2:16][CH2:15][CH2:14]2)=[CH:6][CH:5]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a stirred suspension of sodium hydride (60% susp. in oil, 12.24 g, 255 mmol) in anhydrous DMSO (240 mL) is added dropwise 2-(4-bromophenyl)acetonitrile (20.0 g, 102 mmol) dissolved in anhydrous DMSO (40 mL). After 45 min, the reaction mixture is cooled to 0° C. and 1,3-dibromopropane (30.9 g, 15.5 mL, 153 mmol) dissolved in anhydrous DMSO (40 mL) is added slowly to maintain the temperature below 45° C. The reaction mixture is stirred overnight at room temperature and poured in cold water (1.2 L). The product is extracted with CH2Cl2 (6×100 mL), dried on MgSO4, filtered and concentrated under reduced pressure. The product is purified by flash chromatography eluting with hexane:EtOAc (100% to 95:5) to provide the expected product 1-(4-bromophenyl)cyclobutanecarbonitrile (9.9 g, 41%) as a yellowish oil. 1H NMR (300 MHz, CHLOROFORM-D): δ 7.57-7.49 (2H, m), 7.33-7.24 (2H, m), 2.89-2.77 (2H, m), 2.66-2.34 (3H, m), 2.15-1.99 (1H, m).

Aufarbeitung

additionis added slowly
temperatureto maintain the temperature below 45° C
extractionThe product is extracted with CH2Cl2 (6×100 mL)
customdried on MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe product is purified by flash chromatography
washeluting with hexane

Quellen und Nachweise

ORD-Eintrag: ord-c584fab507c548fc95cc8115d5475cad
Quelldatensatz: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07906654B2

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