Reaction #2320134

Reaction equation

2-(3-bromophenyl)-5-methylpyridine

3-fluorophenylboronic acid

triphenylphosphine

sodium carbonate

→

2-(3′-fluorobiphenyl-3-yl)pyridine

Solvents

water

dimethoxyethane

ethyl acetate

Conditions

Workup

1. 1
   Otherthree-necked round bottom flask equipped with a stir bar
2. 2
   TemperatureThe solution was heated
3. 3
   Temperatureat reflux for twenty hours
4. 4
   Temperaturecooled
5. 5
   OtherThe organic layer was separated
6. 6
   Dryingdried over magnesium sulfate
7. 7
   Otherevaporated to dryness
8. 8
   Otherto give a brown liquid, which
9. 9
   Otherwas purified by flash silica gel chromatography
10. 10
    Otheryielding a viscous, colorless liquid (12.5 g 80%)

Procedure

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