Réaction #2320134

Équation de réaction

2-(3-bromophenyl)-5-methylpyridine

3-fluorophenylboronic acid

triphenylphosphine

sodium carbonate

→

2-(3′-fluorobiphenyl-3-yl)pyridine

Solvants

water

dimethoxyethane

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Autrethree-necked round bottom flask equipped with a stir bar
2. 2
   TempératureThe solution was heated
3. 3
   Températureat reflux for twenty hours
4. 4
   Températurecooled
5. 5
   AutreThe organic layer was separated
6. 6
   Séchagedried over magnesium sulfate
7. 7
   Autreevaporated to dryness
8. 8
   Autreto give a brown liquid, which
9. 9
   Autrewas purified by flash silica gel chromatography
10. 10
    Autreyielding a viscous, colorless liquid (12.5 g 80%)

Mode opératoire

To a 500 mL. three-necked round bottom flask equipped with a stir bar, temperature probe, and a nitrogen inlet were added 2-(3-bromophenyl)-5-methylpyridine (14.7 g, 60 mmol), 3-fluorophenylboronic acid (10.0 g, 72 mmol), palladium (II) acetate (0.335 g, 1.5 mmol), triphenylphosphine (1.56 g, 6.0 mmol), sodium carbonate (17.0 g, 160 mmol), containing dimethoxyethane (120 mL.) and water (80 mL.). The solution was heated at reflux for twenty hours, cooled, and diluted with ethyl acetate. The organic layer was separated, dried over magnesium sulfate, and evaporated to dryness to give a brown liquid, which was purified by flash silica gel chromatography using a 5/95 to 10/90 ethyl acetate/hexane gradient, yielding a viscous, colorless liquid (12.5 g 80%).

Source