Allyltributylstannane → 5-Allyl-2,1,3-benzoxadiazole

HRID 1187089Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1187089
Br[C:2]1[CH:10]=[CH:9][C:5]2=[N:6][O:7][N:8]=[C:4]2[CH:3]=1.[Cl-].[Li+].[CH2:13]([Sn](CCCC)(CCCC)CCCC)[CH:14]=[CH2:15]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:15]([C:2]1[CH:10]=[CH:9][C:5]2=[N:6][O:7][N:8]=[C:4]2[CH:3]=1)[CH:14]=[CH2:13]

Komponenten

6

Edukt 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 27762985-Bromo-2,1,3-benzoxadiazole

Produkt 1

HCID 595687145-Allyl-2,1,3-benzoxadiazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

5-Bromo-2,1,3-benzoxadiazole (10 g, 50.3 mmol) was dissolved in toluene (300 mL) and treated with lithium chloride (6.39 g, 151 mmol), Pd(Ph3P)4 (2.90 g, 2.51 mmol), and allyltributylstannane (18.66 ml, 60.3 mmol). Degassed and refluxed the mixture under N2 for 3 hrs. The reaction mixture turned black. Poured the reaction mixture into water and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried, and evaporated to dryness. The residue was chromatographed through 120 g ISCO Redi-Sep column and eluted with 0-10% ethyl acetate/hexane to yield 5-(prop-2-en-1-yl)-2,1,3-benzoxadiazole.

Aufarbeitung

  1. customDegassed
  2. temperaturerefluxed the mixture under N2 for 3 hrs
  3. additionPoured the reaction mixture into water
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with brine
  7. customdried
  8. customevaporated to dryness
  9. customThe residue was chromatographed through 120 g ISCO Redi-Sep column
  10. washeluted with 0-10% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-4bf0cbdd74214d759c662c6e9f2a2b08
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673920B2

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