Phosphorus tribromide → 4'-(Bromomethyl)-2'-fluorobiphenyl-2-carbonitrile

HRID 519545Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 519545
[F:1][C:2]1[CH:7]=[C:6]([CH2:8]O)[CH:5]=[CH:4][C:3]=1[C:10]1[C:11]([C:16]#[N:17])=[CH:12][CH:13]=[CH:14][CH:15]=1.P(Br)(Br)[Br:19].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Br:19][CH2:8][C:6]1[CH:5]=[CH:4][C:3]([C:10]2[C:11]([C:16]#[N:17])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[C:2]([F:1])[CH:7]=1

Komponenten

5

Edukt 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 670099902'-Fluoro-4'-(hydroxymethyl)biphenyl-2-carbonitrile

Produkt 1

HCID 670084324'-(Bromomethyl)-2'-fluorobiphenyl-2-carbonitrileAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution (150 mL) of 2′-fluoro-4′-(hydroxymethyl)biphenyl-2-carbonitrile (14.1 g) in toluene was added phosphorus tribromide (18.7 g) at room temperature, and the mixture was stirred for 16 hr. Saturated aqueous sodium hydrogen carbonate was added to the reaction mixture, and the solvent was evaporated under reduced pressure, and the residue was extracted with ethyl acetate, and the obtained ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless solid (15.3 g, 100%).

Aufarbeitung

  1. customthe solvent was evaporated under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate
  3. washthe obtained ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a53a4d2f3fbf40a6907ce037e7b0b674
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115136B2

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