1,4-Dioxane → 1,1'-(5,5-Dioxidodibenzo[b,d]thiophene-3,7-diyl)diethanone

HRID 337395Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 337395
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][C:12](Br)=[CH:13][C:8]=3[S:7](=[O:16])(=[O:15])[C:6]=2[CH:17]=1.C([Sn](CCCC)(CCCC)C([O:25][CH2:26][CH3:27])=C)CCC.[O:36]1CCO[CH2:38][CH2:37]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>[O:15]=[S:7]1(=[O:16])[C:6]2[CH:17]=[C:2]([C:37](=[O:36])[CH3:38])[CH:3]=[CH:4][C:5]=2[C:9]2[CH:10]=[CH:11][C:12]([C:26](=[O:25])[CH3:27])=[CH:13][C:8]1=2

Komponenten

5

Edukt 3

HCID 312751,4-DioxaneHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 40718983,7-Dibromo-dibenzothiophene 5,5-dioxide

Produkt 1

HCID 712548711,1'-(5,5-Dioxidodibenzo[b,d]thiophene-3,7-diyl)diethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 3,7-dibromodibenzo[b,d]thiophene 5,5-dioxide (600 mg, 1.604 mmol), Tributyl(1-ethoxyvinyl)tin (2.251 mL, 6.67 mmol) and Pd(Ph3P)4 (185 mg, 0.160 mmol) in 1,4-dioxane (15 mL) were degassed with nitrogen for 10 min then it was heated at 90° C. for overnight under nitrogen. The reaction mixture was cooled to room temperature and 15 mL of 10% HCl was added then stirred for 1 h. The mixture was extracted with ethyl acetate and the organic layer was washed with water and brine. The organics were dried (Na2SO4) and concentrated. The crude material was purified on silica gel using 0-100% ethyl acetate in hexane. The desired fractions were concentrated to give a white solid.

Aufarbeitung

  1. customwere degassed with nitrogen for 10 min
  2. temperatureThe reaction mixture was cooled to room temperature
  3. addition15 mL of 10% HCl was added
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with water and brine
  6. dry with materialThe organics were dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude material was purified on silica gel using 0-100% ethyl acetate in hexane
  9. concentrationThe desired fractions were concentrated
  10. customto give a white solid

Quellen und Nachweise

ORD-Eintrag
ord-2e4ea2ef856c4460b8fd5e86563755c3
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889726B2

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