1,2-Dimethoxyethane → 2,3',5-Trimethyl-1,1'-biphenyl

HRID 382122

Reaktionsgleichung

Reaktionsgleichung von HRID 382122
C(=O)([O-])[O-].[Na+].[Na+].CC1C=[CH:12][C:11]([CH:14]([C:20]2[CH:25]=[CH:24][C:23](C)=[CH:22][CH:21]=2)[C:15](=O)[CH:16]([CH3:18])[CH3:17])=[CH:10]C=1.[CH3:27]OCCOC.BrC1C=CC=CC=1I>CCOCC.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.C(O)C>[CH3:12][C:11]1[CH:10]=[CH:18][C:16]([CH3:17])=[CH:15][C:14]=1[C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([CH3:27])[CH:25]=1

Komponenten

9

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 114151-Bromo-2-iodobenzeneHCID 120407443-Methyl-1,1-bis(4-methylphenyl)-2-butanone

Produkt 1

HCID 110416892,3',5-Trimethyl-1,1'-biphenylAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

An oven-dried Schlenk flask was cooled to room temperature under an argon purge, and was charged with tetrakis(triphenylphosphine)palladium (289 mg, 0.25 mmol, 5 mol %) sodium carbonate (2.86 g, 27 mmol), and 1 (1.0 g, 5.0 mmol). The flask was purged with argon and DME (50 mL), ethanol (2 mL), water (15 mL), and 2-bromoiodobenzene (0.83 mL, 6.05 mmol) were added through a rubber septem. The mixture was heated to 85° C. with stirring for 3 days. The mixture was cooled to room temperature, diluted with ether (100 mL), and poured into a separatory funnel. The layers were separated and the organic phase was washed with 1M NaOH (2×50 mL), washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel to afford 1.23 g (79%) of 2 as a colorless oil.

Aufarbeitung

  1. custompurge
  2. additionwere added through a rubber septem
  3. temperatureThe mixture was heated to 85° C.
  4. temperatureThe mixture was cooled to room temperature
  5. additionpoured into a separatory funnel
  6. customThe layers were separated
  7. washthe organic phase was washed with 1M NaOH (2×50 mL)
  8. washwashed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe crude material was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-62f12661d3664b1a8edd386db630f7ba
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06307087B1

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