Phosphorus tribromide → 4-(3-Bromopropoxy)-3-fluorobenzonitrile

HRID 1992380Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1992380
P(Br)(Br)[Br:2].[F:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][CH2:17]O)[C:9]#[N:10]>C(Cl)(Cl)(Cl)Cl>[Br:2][CH2:17][CH2:16][CH2:15][O:14][C:13]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[F:5]

Komponenten

4

Edukt 2

HCID 24614Phosphorus tribromideHCID 436575093-Fluoro-4-(3-hydroxypropoxy)-benzonitrile

Produkt 1

HCID 685196304-(3-Bromopropoxy)-3-fluorobenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

PBr3 (8.14 g, 0.03 mol) was added drop by drop at 0° C. to a solution of 3-fluoro-4-(3-hydroxypropoxy)-benzonitrile (5.5 g, 0.028 mol, from step (i) above in carbon tetrachloride (50 ml) and stirred at room temperature overnight under nitrogen atmosphere. The reaction was quenched with water, and extracted with dichloromethane. Organic layer was washed with water, brine, dried over sodium sulfate and solvent evaporated under reduced pressure. The residue was purified by column chromatography over silica gel using 6% ethyl acetate in petroleum ether as eluent to yield (4.3 g) of the title compound as a liquid.

Aufarbeitung

  1. customThe reaction was quenched with water
  2. extractionextracted with dichloromethane
  3. washOrganic layer was washed with water, brine
  4. dry with materialdried over sodium sulfate and solvent
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography over silica gel using 6% ethyl acetate in petroleum ether as eluent

Quellen und Nachweise

ORD-Eintrag
ord-1d2dae3589bc46c1908b7b75f3d0e759
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07648985B2

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