Potassium Phosphate, Tribasic → 4-Methyldibenzo[b,d]furan

HRID 717990

Reaktionsgleichung

Reaktionsgleichung von HRID 717990
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]B1OB(C)OB(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>[CH3:23][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

Komponenten

8

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 4582574-IododibenzofuranHCID 574072Trimethylboroxine

Produkt 1

HCID 434894-Methyldibenzo[b,d]furanAusbeute 554,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

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

Versuchsvorschrift

4-Iododibenzo[b,d]furan (10 g, 34.0 mmol) and potassium phosphate (23.49 g, 102 mmol) were dissolved in 200 mL of toluene and 20 mL of water. The reaction was purged with nitrogen for 20 minutes and then 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (5.34 mL, 5.94 mmol), Pd2(dba)3 (0.311 g, 0.34 mmol) and S-Phos (0.558 g, 1.36 mmol) were added. The reaction was refluxed for 18 hours. After allowing the reaction to cool to room temperature, 100 mL of water was added, the organic and aqueous layers were separated, and the aqueous layer extracted twice with 100 mL of toluene. 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 6 g (96.7%) pure product which was confirmed GC.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-7cb3671deae64fd89ec0c2f9db78670f
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193745B2

Verknüpfte Notizen

Wird geladen…