Potassium Phosphate, Tribasic → 4-(Prop-1-en-2-yl)dibenzo[b,d]furan

HRID 717991

Reaktionsgleichung

Reaktionsgleichung von HRID 717991
I[C:2]1[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:23][C:24]1(C)[C:28](C)(C)OB(C(C)=C)O1>C1(C)C=CC=CC=1.O.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].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>[CH2:23]=[C:24]([C:2]1[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH3:28]

Komponenten

8

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 4582574-IododibenzofuranHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane

Produkt 1

HCID 177536004-(Prop-1-en-2-yl)dibenzo[b,d]furanAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylKatalysatorHCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittel

Versuchsvorschrift

4-Iododibenzo[b,d]furan (25 g, 85.0 mmol) and potassium phosphate (58.7 g, 255 mmol) were dissolved in 500 mL of toluene and 50 mL of water. The reaction was purged with nitrogen for 20 minutes and then 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (15.98 mL, 85 mmol), Pd2(dba)3 (1.55 g, 1.7 mmol) and S-Phos (2.79 g, 6.8 mmol) were added. The reaction was refluxed for 18 hours. After cooling the reaction to room temperature, 100 mL of water was added, the organic and aqueous layers were separated, and the aqueous layer was extracted twice with 100 mL of ethyl acetate. The organic layers were passed through a plug of silica gel, eluting with DCM. After evaporation of the solvent, the crude product was subjected to column chromatography (SiO2, 3% ethyl acetate in hexane to 5% ethyl acetate in hexane, v/v) to yield 14.5 g (82%) of pure product.

Aufarbeitung

  1. customThe reaction was purged with nitrogen for 20 minutes
  2. temperatureThe reaction was refluxed for 18 hours
  3. temperatureAfter cooling
  4. customthe reaction to room temperature
  5. customthe organic and aqueous layers were separated
  6. extractionthe aqueous layer was extracted twice with 100 mL of ethyl acetate
  7. washeluting with DCM
  8. customAfter evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-3813ada44f0e49d98ff94d8e963f66bb
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193745B2

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