1,5-Dibromopentane → 1-(3,4-Difluorophenyl)cyclohexanecarbonitrile

HRID 71233Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 71233
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[F:8].[H-].[Na+].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([C:10]#[N:11])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:5]=[CH:6][C:7]=1[F:8]

Komponenten

5

Edukt 3

HCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 69572(3,4-Difluorophenyl)acetonitrile

Produkt 1

HCID 666852131-(3,4-Difluorophenyl)cyclohexanecarbonitrileAusbeute 87,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 2-(3,4-difluorophenyl)acetonitrile (2 g, 13.06 mmol) in 20 mL of DMF at 0° C. was added 60% sodium hydride (1.149 g, 28.7 mmol), and the mixture was stirred at the same temperature for 5 mins. Then a solution of 1,5-dibromopentane (1.779 mL, 13.06 mmol) in 20 mL of DMF was added dropwise and the mixture was stirred at a temperature in the range 0° C. to room temperature for 5 hrs. The reaction was quenched with water, and extracted with EtOAc. The mixture was washed with water and brine. The combined aqueous layers were back extracted with EtOAc once and washed with brine. The combined extracts were dried over Na2SO4 and evaporated to give an oily residue. It was purified by Combiflash (120 g silica gel) eluting with 1:9 EtOAc-hexane to give 1-(3,4-difluorophenyl)cyclohexanecarbonitrile (2.52 g, 11.39 mmol, 87% yield). 1H NMR (400 MHz, CCl3D) δ ppm 7.12-7.35 (3H, m), 2.14 (2H, d, J=11.86 Hz), 1.75-1.95 (6H, m), 1.64-1.75 (2H, m).

Aufarbeitung

  1. stirringthe mixture was stirred at a temperature in the range 0° C. to room temperature for 5 hrs
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. washThe mixture was washed with water and brine
  5. extractionThe combined aqueous layers were back extracted with EtOAc once
  6. washwashed with brine
  7. dry with materialThe combined extracts were dried over Na2SO4
  8. customevaporated
  9. customto give an oily residue
  10. customIt was purified by Combiflash (120 g silica gel)
  11. washeluting with 1:9 EtOAc-hexane

Quellen und Nachweise

ORD-Eintrag
ord-6fa4215e2b984d9cb9c36bff7b82f2f4
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822510B2

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