Sodium Carbonate → 2-(6-Methyl-2-naphthyl)benzaldehyde

HRID 2112370

Reaktionsgleichung

Reaktionsgleichung von HRID 2112370
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:12])[CH:8]=2)[CH:3]=1.[CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O)=[O:14].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC>[CH3:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH:13]=[O:14])[CH:11]=[CH:10]2

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 2921892-Formylphenylboronic acidHCID 6405922-Bromo-6-methylnaphthalene

Produkt 1

HCID 862261722-(6-Methyl-2-naphthyl)benzaldehydeAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

Under an atmospheric argon gas flow, 2-bromo-6-methylnaphthalene in an amount of 6.6 g (30 mmol), 2-formylphenylboronic acid in an amount of 5.4 g (36 mmol), (tetrakistriphenylphosphine)palladium in an amount of 0.7 g (0.6 mmol), 2N sodium carbonate aqueous solution in an amount of 45 milliliter and dimethoxyethane in an amount of 90 milliliter were placed into a three neck flask with a cooling pipe and having a capacity of 500 milliliter, and the resultant solution was refluxed under heating for 8 hours. After the reaction terminated, adding water in an amount of 100 milliliter into the reacted solution, an organic layer was separated and washed with the use of sodium chloride solution, followed by drying with the use of magnesium sulfate. After removing the solvent by distillation by means of a rotary evaporator, the resultant crude product was refined by means of column chromatography (silicagel, hexane/dichloromethane=60/40), and as a result, 6.7 g of aimed compound (white crystal) was obtained (yield: 91%).

Aufarbeitung

  1. temperatureunder heating for 8 hours
  2. customAfter the reaction terminated
  3. additionadding water in an amount of 100 milliliter into the reacted solution
  4. customan organic layer was separated
  5. washwashed with the use of sodium chloride solution
  6. dry with materialby drying with the use of magnesium sulfate
  7. customAfter removing the solvent
  8. distillationby distillation
  9. customby means of a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-bf63b4d967b941bb88d5111e67ad6290
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07524568B2

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