Reacción #2075718

Ecuación de reacción

Bis(2-methoxyethyl)aminosulfur trifluoride

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

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title compound

Rendimiento 65.8%

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

Rendimiento 65.8%

Disolventes

water

dichloromethane

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente