Реакция #41915

Уравнение реакции

tris(2-bromo-6-pyridyl)methanol

diethylaminosulfur trifluoride

sodium hydroxide

→

Tris(2-bromo-6-pyridyl)fluoromethane

Растворители

dichloromethane

water

water

Условия реакции

Обработка

1. 1
   ТемператураSubsequently, the reaction mixture was heated
2. 2
   Температураunder reflux for 30 min
3. 3
   ДругоеThe organic phase was removed
4. 4
   Промывкаthe aqueous phase was washed twice with 200 ml of dichloromethane
5. 5
   Сушкаthe combined organic phases were dried over calcium chloride
6. 6
   Фильтрацияfiltered off
7. 7
   ПромывкаAfter washing with methanol
8. 8
   Другоеthe colorless to beige crystals were dried under reduced pressure

Методика

A solution of 50.0 g (100 mmol) of tris(2-bromo-6-pyridyl)methanol in 750 ml of dichloromethane was admixed with good stirring dropwise with 47.3 ml (400 mmol) of diethylaminosulfur trifluoride. Subsequently, the reaction mixture was heated under reflux for 30 min, then cooled to 5° C., and admixed with good stirring (highly exothermic!!!) with 300 ml of water and then with a solution of 64.0 g (1600 mmol) of sodium hydroxide in 600 ml of water (highly exothermic!!!). The organic phase was removed, the aqueous phase was washed twice with 200 ml of dichloromethane, and the combined organic phases were dried over calcium chloride and subsequently freed of dichloromethane. The remaining red-brown crystal slurry was taken up in 100 ml of methanol and filtered off. After washing with methanol, the colorless to beige crystals were dried under reduced pressure. The yield was 47.4 g (91.3%) at a purity of greater than 99.0% by 1H NMR.

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