Reaktion #58859

Reaktionsgleichung

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

diethylamino sulfur trifluoride

water

→

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

Ausbeute 63.0%

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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]+.

Quelle