Allyl bromide → 4-(Allyloxy)-5-bromo-2-chlorobenzonitrile

HRID 2206693

Reaktionsgleichung

Reaktionsgleichung von HRID 2206693
[Br:1][C:2]1[C:3]([OH:11])=[CH:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[CH2:12](Br)[CH:13]=[CH2:14].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:14]([O:11][C:3]1[C:2]([Br:1])=[CH:9][C:6]([C:7]#[N:8])=[C:5]([Cl:10])[CH:4]=1)[CH:13]=[CH2:12]

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 533304525-Bromo-2-chloro-4-hydroxybenzonitrile

Produkt 1

HCID 867140364-(Allyloxy)-5-bromo-2-chlorobenzonitrileAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of compound 37 (20.5 g, 88.1 mmol), allyl bromide (11.2 mL, 132 mmol) and K2CO3 (24.4 g, 176 mmol) in acetone (440 mL) was stirred for 3 hours under reflux. The mixture was filtrated and concentrated in vacuo. The resultant was partitioned between EtOAc and water. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to afford the product 38 (15.6 g, 65%) as a white solid.

Aufarbeitung

  1. temperatureunder reflux
  2. filtrationThe mixture was filtrated
  3. concentrationconcentrated in vacuo
  4. customThe resultant was partitioned between EtOAc and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bdbbee18eaab4fd48597365336264816
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09371303B2

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