반응 #2075718

반응 방정식

Bis(2-methoxyethyl)aminosulfur trifluoride

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

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title compound

수율 65.8%

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

수율 65.8%

용매

water

dichloromethane

반응 조건

후처리

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

실험 절차

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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