Water → 3-(3-Bromopropyl)benzonitrile

HRID 1093467Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1093467
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11]O)[CH:6]=[CH:7][CH:8]=1)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:32]N1C(=O)CCC1=O.O>C(Cl)Cl>[Br:32][CH2:11][CH2:10][CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 138542623-(3-Hydroxypropyl)benzonitrile

Produkt 1

HCID 193772303-(3-Bromopropyl)benzonitrileAusbeute 87,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Compound 75-2 (4.45 g) was dissolved in methylene chloride (95 ml), triphenylphosphine (8.13 g) and N-bromosuccinimide (5.51 g) were added under ice-cooling, and the mixture was stirred under ice-cooling for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with methylene chloride and washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. Diethyl ether was added, and the precipitated triphenylphosphine oxide was filtered off. The concentrate of the filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give the object product (5.44 g) as a colorless oil.

Aufarbeitung

  1. temperaturecooling
  2. temperaturecooling for 2 hr
  3. extractionthe mixture was extracted with methylene chloride
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. additionDiethyl ether was added
  8. filtrationthe precipitated triphenylphosphine oxide was filtered off
  9. concentrationThe concentrate of the filtrate
  10. customwas purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-2ce83bba533146bea27d7d6c1ed127ec
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129361B2

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