2,3-Dibromobutane → 1-[4-(Trifluoromethoxy)phenyl]cyclopentanecarbonitrile

HRID 404603

Reaktionsgleichung

Reaktionsgleichung von HRID 404603
[H-].[Na+].[F:3][C:4]([F:16])([F:15])[O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]#[N:14])=[CH:8][CH:7]=1.Br[CH:18]([CH:20](Br)[CH3:21])[CH3:19]>C1COCC1>[F:3][C:4]([F:15])([F:16])[O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2([C:13]#[N:14])[CH2:21][CH2:20][CH2:18][CH2:19]2)=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 215082,3-DibromobutaneHCID 24758Sodium hydrideHCID 1426764-(Trifluoromethoxy)phenylacetonitrile

Produkt 1

HCID 595365491-[4-(Trifluoromethoxy)phenyl]cyclopentanecarbonitrileAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To sodium hydride (600 mg, 15 mmol) in anhydrous THF (5 mL) at 0° C., was added dropwise 2-(4-(trifluoromethoxy)phenyl)acetonitrile (1006 mg, 5 mmol) and then the reaction mixture was stirred for 5 mins, followed by dibromobutane (1075 mg, 5 mmol) dropwise. The reaction mixture was heated to reflux for 16 h, then cooled to 0° C., quenched with MeOH (1 mL), diluted with EtOAC (50 mL) and washed with brine (3×50 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to give 1-(4-(trifluoromethoxy)phenyl)cyclopentanecarbonitrile as a yellow oil (905 mg, 71%) (1H NMR (400 MHz, CDCl3) 7.50 (dd, J=2.1, 6.7 Hz, 2H), 7.25 (d, J=8.2 Hz, 2H), 2.53-2.49 (m, 2H), 2.10-1.97 (m, 6H)

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 16 h
  3. customquenched with MeOH (1 mL)
  4. additiondiluted with EtOAC (50 mL)
  5. washwashed with brine (3×50 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fc28b615a66e438caf1a979ba3d8585a
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748612B2

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