Dichloromethane → 5-Benzyl-3H-isobenzofuran-1-one

HRID 706174

Reaktionsgleichung

Reaktionsgleichung von HRID 706174
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[O:6][CH2:5]2.[Br-].[CH2:13]([Zn+])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(Cl)Cl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[CH2:13]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[O:6][CH2:5]2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

6

Edukt 3

HCID 6344DichloromethaneHCID 6031445-BromophthalideHCID 178419772HCID 178419772, Verbindung

Produkt 1

HCID 584166365-Benzyl-3H-isobenzofuran-1-oneAusbeute 43,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 5-bromo-3H-isobenzofuran-1-one (14 mmol, 3.04 g), benzylzinc bromide solution (0.5 M in THF, 28 mmol, 56 mL), [1,1′bis(diphenylphosphino)-ferrocene]dichloropalladium(II) 1:1 complex with CH2Cl2 (0.07 mmol, 57 mg), and anhydrous 1.4-dioxane (70 mL) was refluxed with stirring under nitrogen for 40 h. After cooling to ambient temperature silica gel was added and the mixture was concentrated in vacuo. The residue was added on top of a chromatography column filled with silica gel. Elution with hexanes:ethyl acetate=9:1 gave a yellow solid. Further purification by recrystallization from ethyl acetate/hexanes gave the title compound (1.37 g) as white needles; 1H NMR (CDCl3, 200 MHz): δ=7.83 (d, 1H), 7.16 to 7.39 (m, 7H), 5.26 (s, 2H), 4.11 (s, 2H).

Aufarbeitung

  1. temperaturewas refluxed
  2. additionwas added
  3. concentrationthe mixture was concentrated in vacuo
  4. additionThe residue was added on top of a chromatography column
  5. additionfilled with silica gel
  6. washElution with hexanes
  7. customethyl acetate=9:1 gave a yellow solid
  8. customFurther purification
  9. customby recrystallization from ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-45552c40f96d4f20b95aa36c9fb6802e
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174976B2

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