Reaktion #2075718

Reaktionsgleichung

Bis(2-methoxyethyl)aminosulfur trifluoride

1-(5-bromo-2-chlorophenyl)ethanol

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title compound

Ausbeute 65.8%

4-Bromo-1-chloro-2-(1-fluoro-ethyl)-benzene

Ausbeute 65.8%

Lösungsmittel

water

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was quenched with a 5% solution of aquous sodium bicarbonate (100 mL)
2. 2
   Sonstigethe resulting bubbling
3. 3
   Sonstigebiphasic reaction mixture
4. 4
   workup.STIRRINGwas vigorously stirred at 0° C. for 15 m
5. 5
   Extraktionextracted with dichloromethane twice
6. 6
   WaschenThe combined organic layers were washed with 1M hydrochloric acid
7. 7
   Sonstigedried
8. 8
   Einengenconcentrated by rotary evaporation
9. 9
   SonstigeThe product was purified by flash chromatography on silica gel (hexanes)

Vorschrift

Bis(2-methoxyethyl)aminosulfur trifluoride (4.5 g, 20.34 mmol) was added to a stirred solution of 1-(5-bromo-2-chlorophenyl)ethanol (3.99 g, 16.95 mmol) in dichloromethane (50 mL) at 0° C. The resulting solution was stirred at 0° C. for 3 h. The reaction mixture was quenched with a 5% solution of aquous sodium bicarbonate (100 mL) and the resulting bubbling biphasic reaction mixture was vigorously stirred at 0° C. for 15 m. The reaction mixture was diluted with water (50 mL) and extracted with dichloromethane twice. The combined organic layers were washed with 1M hydrochloric acid, dried and concentrated by rotary evaporation. The product was purified by flash chromatography on silica gel (hexanes) to yield the title compound (2.65 g, 11.16 mmol, 65.8% yield) as a clear oil: 1H NMR (CDCl3): δ 7.65 (d, 1H), 7.37 (m, 1H), 7.20 (m, 1H), 5.88 (dq, 1H), 1.61 (dd, 3H).

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