Реакция #2320134

Уравнение реакции

2-(3-bromophenyl)-5-methylpyridine

3-fluorophenylboronic acid

triphenylphosphine

sodium carbonate

→

2-(3′-fluorobiphenyl-3-yl)pyridine

Растворители

water

dimethoxyethane

ethyl acetate

Условия реакции

Обработка

1. 1
   Другоеthree-necked round bottom flask equipped with a stir bar
2. 2
   ТемператураThe solution was heated
3. 3
   Температураat reflux for twenty hours
4. 4
   Температураcooled
5. 5
   ДругоеThe organic layer was separated
6. 6
   Сушкаdried over magnesium sulfate
7. 7
   Другоеevaporated to dryness
8. 8
   Другоеto give a brown liquid, which
9. 9
   Другоеwas purified by flash silica gel chromatography
10. 10
    Другоеyielding a viscous, colorless liquid (12.5 g 80%)

Методика

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%).

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