Potassium Persulfate → 4-Bromo-2,3-dihydro-2,2-dimethyl-3-benzofuranone

HRID 52656

Reaktionsgleichung

Reaktionsgleichung von HRID 52656
[Br:1][C:2]1[C:7]2[CH2:8][C:9]([CH3:12])([CH3:11])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.S(OOS([O-])(=O)=O)([O-])(=O)=[O:14].[K+].[K+]>O.C(#N)C.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[Br:1][C:2]1[C:7]2[C:8](=[O:14])[C:9]([CH3:12])([CH3:11])[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 2

HCID 24412Potassium PersulfateHCID 539891274-Bromo-2,2-dimethyl-2,3-dihydrobenzofuran

Produkt 1

HCID 543779064-Bromo-2,3-dihydro-2,2-dimethyl-3-benzofuranoneAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24463Copper sulfate pentahydrateKatalysatorHCID 962WaterLösungsmittel2×HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, a stirred solution of 3.0 grams (0.013 mole) 4-bromo-2,3-dihydro-2,2-dimethylbenzofuran, 10.7 grams (0.039 mole) of potassium persulfate, and 3.3 grams (0.013 mole) of copper(II) sulfate pentahydrate in 30 mL of water and 30 mL of acetonitrile was heated at reflux for one hour. After this time the reaction mixture was poured into 200 mL of water. The mixture was then extracted with one 200 mL portion of diethyl ether. The extract was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The oil was subjected to column chromatography on silica gel. Elution was accomplished using 1:1 petroleum ether and methylene chloride. The product-containing fractions were combined and concentrated under reduced pressure, yielding 2.1 grams of 4-bromo-2,3-dihydro-2,2-dimethyl-3-benzofuranone. The NMR spectrum was consistent with the proposed structure. Steps A through C were repeated.

Aufarbeitung

  1. temperatureat reflux for one hour
  2. extractionThe mixture was then extracted with one 200 mL portion of diethyl ether
  3. dry with materialThe extract was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
  6. washElution
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3fbbd22283364d73a3e65ae42d09c7e0
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616718

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