1,2-Dibromoethane → 1-(4-Bromo-3-fluorophenyl)cyclopropane-1-carbonitrile

HRID 910879Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 910879
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][C:3]=1[F:11].Br[CH2:13][CH2:14]Br.[OH-].[Na+]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:9]#[N:10])[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:11]

Komponenten

7

Edukt 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 116009532-(4-Bromo-3-fluorophenyl)acetonitrile

Produkt 1

HCID 117156671-(4-Bromo-3-fluorophenyl)cyclopropane-1-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 4-bromo-3-fluorophenylacetonitrile (5 g, 23 mmoles) in toluene (20 ml) is added with 35 mmoles of 1,2-dibromoethane, a 50% NaOH aqueous solution (20 ml) and tetrabutylammonium bromide (1.6 g, 5 mmoles). The mixture is kept under stirring at room temperature for 5-12 hours, then diluted with water and extracted with ethyl acetate. The organic phase is washed with 1N HCl, then with brine, finally dried and concentrated under vacuum to give a brown solid, which is subjected to chromatography on a silica gel column (200 g), eluting with hexane-ethyl ether 1-1, to afford the product in the solid form.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with 1N HCl
  3. dry with materialwith brine, finally dried
  4. concentrationconcentrated under vacuum
  5. customto give a brown solid, which
  6. washeluting with hexane-ethyl ether 1-1
  7. customto afford the product in the solid form

Quellen und Nachweise

ORD-Eintrag
ord-5812937b96094cd88bc431191e21a3d2
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022250B2

Notizen zur Reaktion

Wird geladen…