Реакция #68976

Уравнение реакции

4-Bromophenol

Sodium hydride

HCl

2-fluoropyridine

→

2-(4-bromo-phenoxy)pyridine

Выход 77.2%

Растворители

DMF

Условия реакции

Обработка

1. 1
   Температураthe reaction medium is heated at 105° C. for 7 h
2. 2
   ДругоеAfter hydrolysis
3. 3
   ЭкстракцияThe reaction medium is then extracted with ethyl acetate
4. 4
   ПромывкаThe organic phase is washed with a saturated aqueous sodium chloride solution
5. 5
   Сушкаdried over MgSO4
6. 6
   Концентрированиеconcentrated to dryness
7. 7
   ДругоеThe crude product obtained
8. 8
   Другоеis chromatographed on silica gel, elution

Методика

4-Bromophenol (2 g, 11.5 mmol) is placed in 10 ml of anhydrous DMF under nitrogen. Sodium hydride (0.51 g, 127 mmol) is added. After stirring for 20 min at ambient temperature, 2-fluoropyridine (1.05 ml, 12.1 mmol) is added and the reaction medium is heated at 105° C. for 7 h. After hydrolysis, the pH is adjusted to 8 with a 1N aqueous solution of HCl. The reaction medium is then extracted with ethyl acetate. The organic phase is washed with a saturated aqueous sodium chloride solution, dried over MgSO4 and concentrated to dryness. The crude product obtained is chromatographed on silica gel, elution being carried out with a gradient of ethyl acetate in heptane ranging from 0% to 30%. 2.22 g of expected 2-(4-bromo-phenoxy)pyridine are obtained,

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