Phenol → 4-Bromo-2-phenoxybenzonitrile

HRID 425270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 425270
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O-]C1C=CC=CC=1.[Br:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[C:20](F)[CH:19]=1.[OH-].[Na+]>CN(C=O)C>[Br:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[C:20]([O:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:19]=1

Komponenten

7

Edukt 5

HCID 996PhenolHCID 14798Sodium HydroxideHCID 24758Sodium hydride2×HCID 119047PhenolateHCID 7360294-Bromo-2-fluorobenzonitrile

Produkt 1

HCID 574366654-Bromo-2-phenoxybenzonitrileAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (12 g, 300 mmol) (60% by wt) was weighed into a flask and washed free of oil with several hexane rinsings. The hexanes were decanted and discarded and DMF was added to the flask. A DMF-solution of phenol (23.5 g, 250 mmol in 100 mL DMF) was added dropwise to the NaH mixture and stirred at room temperature. To the phenoxide was added a solution of 4-bromo-2-fluoro-benzonitrile (50 g, 250 mmol in 100 mL DMF), dropwise. Upon complete addition, the reaction was refluxed for 20 h. The reaction was cooled to room temperature, and poured into cold 1 N NaOH. A fine, tan precipitate formed and was collected by vacuum filtration to give 62.04 g (226 mmol) of Compound 1a. MS m/z (MH+) 277.

Aufarbeitung

  1. washwashed free of oil with several hexane rinsings
  2. customThe hexanes were decanted
  3. additionDMF was added to the flask
  4. additionUpon complete addition
  5. temperaturethe reaction was refluxed for 20 h
  6. temperatureThe reaction was cooled to room temperature
  7. customA fine, tan precipitate formed
  8. filtrationwas collected by vacuum filtration

Quellen und Nachweise

ORD-Eintrag
ord-a698c13d334646439e984657462f286a
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106207B2

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