Diethyl Ether → HCID 89851679, Verbindung

HRID 1771433Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1771433
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([F:12])([F:11])[F:10].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C([O:28][CH2:29][CH3:30])C.[F-].[K+]>C1(C)C=CC=CC=1.C([Sn](CCCC)(CCCC)C=C)CCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CCCCC>[F:10][C:9]([F:12])([F:11])[CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:30]1[CH2:29][O:28]1

Komponenten

9

Edukt 4

HCID 3283Diethyl EtherHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 522689Potassium FluorideHCID 457904731-Bromo-2-(2,2,2-trifluoroethyl)benzene

Produkt 1

HCID 89851679HCID 89851679, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 8003PentaneLösungsmittelHCID 81998TributylvinyltinLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Bromo-2-(2,2,2-trifluoroethyl)benzene (0.5 g) was dissolved in degassed toluene and tributyl(vinyl)tin (0.67 mL), Pd2(dba)3 (0.096 g) and tri-tert-butylphosphine (0.25 mL, 1M solution) were added. Reaction mixture was heated to 40° C. After 4 hours heating was stopped and 1:1 solution of diethyl ether and pentane (10 ml) was added, followed by potassium fluoride (1.0 g). Mixture was stirred for 30 minutes after which it was filtered through a pad of silicagel and the filtrate was concentrated gently at 500 mbar vacuum. The evaporation residue was purified by column chromatography (diethyl ether-pentane) and fractions containing the product were concentrated by house vacuum distillation. The evaporation residue (0.389 g) containing toluene and the desired styrene product was dissolved in dichloromethane (12 mL) and 3-chloroperoxybenzoic acid (0.70 g) was added.

Aufarbeitung

  1. customReaction mixture
  2. temperatureAfter 4 hours heating
  3. filtrationwas filtered through a pad of silicagel
  4. concentrationthe filtrate was concentrated gently at 500 mbar vacuum
  5. customThe evaporation residue was purified by column chromatography (diethyl ether-pentane) and fractions
  6. additioncontaining the product
  7. concentrationwere concentrated by house vacuum distillation
  8. additionThe evaporation residue (0.389 g) containing toluene
  9. dissolutionthe desired styrene product was dissolved in dichloromethane (12 mL)
  10. addition3-chloroperoxybenzoic acid (0.70 g) was added

Quellen und Nachweise

ORD-Eintrag
ord-acad2e6cefae4a1bb3ca2925ff9b7393
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249127B2

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