Реакция #315057

Уравнение реакции

phenylboronic acid

potassium fluoride

2-bromo-m-xylene

→

title compound

Выход 79.0%

2,6-dimethylbiphenyl

Выход 79.0%

Растворители

THF

Условия реакции

Обработка

1. 1
   ДругоеAn oven dried resealable Schlenk tube
2. 2
   Другоеwas evacuated
3. 3
   ДругоеThe tube was evacuated
4. 4
   workup.ADDITIONwere added through a rubber septum
5. 5
   Другоеhad been completely consumed
6. 6
   workup.ADDITIONThe reaction mixture was then diluted with ether (30 mL)
7. 7
   Фильтрацияfiltered through celite
8. 8
   Концентрированиеconcentrated
9. 9
   ДругоеThe crude material was purified by flash chromatography on silica gel

Методика

An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol %), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol %), phenylboronic acid (183 mg, 1.5 mmol), and potassium fluoride (174 mg, 3.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) and 2-bromo-m-xylene (0.144 mL, 1.0 mmol) were added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at 65° C. until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 144 mg (79%) of the title compound.

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