Reaktion #59835

Reaktionsgleichung

sodium carbonate

2-bromo-6-methylnaphthalene

2-formylphenylboronic acid

→

aimed compound

Ausbeute 91.0%

2-(6-methyl-2-naphthyl)benzaldehyde

Ausbeute 91.0%

Lösungsmittel

dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder heating for 8 hours
2. 2
   SonstigeAfter the reaction terminated
3. 3
   workup.ADDITIONadding water in an amount of 100 milliliter into the reacted solution
4. 4
   Sonstigean organic layer was separated
5. 5
   Waschenwashed with the use of sodium chloride solution
6. 6
   Trocknenby drying with the use of magnesium sulfate
7. 7
   SonstigeAfter removing the solvent
8. 8
   workup.DISTILLATIONby distillation
9. 9
   Sonstigeby means of a rotary evaporator

Vorschrift

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%).

Quelle