Réaction #2075718

Équation de réaction

Bis(2-methoxyethyl)aminosulfur trifluoride

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

→

title compound

Rendement 65.8%

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

Rendement 65.8%

Solvants

water

dichloromethane

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source