1,2-Dibromoethane → HCID 67179206, Verbindung

HRID 1026142Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1026142
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[F:8].Br[CH2:13][CH2:14]Br.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:10]#[N:11])[CH2:14][CH2:13]2)[CH:5]=[CH:6][C:7]=1[F:8]

Komponenten

6

Edukt 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 27737253-Chloro-4-fluorobenzyl cyanide

Produkt 1

HCID 67179206HCID 67179206, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of 3-chloro-4-fluoro-phenylacetonitrile (8.48 g), 1,2-dibromoethane (13 ml) and benzyltriethylammonium chloride (0.46 g) was added sodium hydroxide solution (50% in water, 20 ml) at room temperature. The mixture was vigorously stirred overnight. Water was added and the aqueous phase was extracted twice with diethyl ether. The combined organic layers were washed with water and brine, dried over MgSO4 and concentrated. The residue was purified by column chromatography (SiO2; heptane/EtOAc) to give 1-(3-chloro-4-fluorophenyl)-cyclopropanecarbonitrile as light yellow liquid (3.91 g). 1H-NMR (300 MHz, CDCl3, δ): 1.35-1.40 (m, 2H), 1.72-1.76 (m, 2H), 7.10-7.21 (m, 2H), 7.26-7.34 (m, 1H).

Aufarbeitung

  1. extractionthe aqueous phase was extracted twice with diethyl ether
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (SiO2; heptane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-1e642f8ae77f4603a3cfe5a8d2d15b77
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729113B2

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