Reaction #2075718

Reaction equation

Bis(2-methoxyethyl)aminosulfur trifluoride

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

→

title compound

Yield 65.8%

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

Yield 65.8%

Solvents

water

dichloromethane

Conditions

Workup

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

Procedure

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