Реакция #58859

Уравнение реакции

5-(3-bromophenyl)pentan-1-ol

diethylamino sulfur trifluoride

water

→

1-bromo-3-(5-fluoropentyl)benzene

Выход 63.0%

Растворители

methylene chloride

methylene chloride

Условия реакции

Обработка

1. 1
   Экстракцияextracted with ether
2. 2
   ПромывкаThe extracts were combined washed sequentially with saturated sodium bicarbonate and water
3. 3
   Сушкаdried over magnesium sulfate
4. 4
   Концентрированиеconcentrated under reduced pressure
5. 5
   ДругоеThe concentrate was purified by flash chromatography on silica gel, 40:1 hexane/ethyl acetate as eluent

Методика

A solution of 5-(3-bromophenyl)pentan-1-ol (0.63 g, 2.6 mmol) in methylene chloride at −78° C. was treated with a solution of diethylamino sulfur trifluoride (DAST) (0.7 mL, 5.2 mmol) in methylene chloride, allowed to warm to room temperature, stirred for 0.5 h at room temperature, poured into water and extracted with ether. The extracts were combined washed sequentially with saturated sodium bicarbonate and water, dried over magnesium sulfate and concentrated under reduced pressure. The concentrate was purified by flash chromatography on silica gel, 40:1 hexane/ethyl acetate as eluent to give 1-bromo-3-(5-fluoropentyl)benzene as a pale yellow oil, 0.4 g (63% yield); 1H NMR (DMSO-d6) δ 1.3 (m, 2H); 1.6 (m, 4H); 2.5 (t, 2 H); 4.4 (dxt, 2H); 7.2 (m, 2 H); 7.4 (m, 2 H); MS [(+)ESI] m/z=245 [M−H]+.

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