反应 #2075718

反应方程式

Bis(2-methoxyethyl)aminosulfur trifluoride

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

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title compound

收率 65.8%

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

收率 65.8%

溶剂

water

dichloromethane

反应条件

后处理

1. 1
   其他The reaction mixture was quenched with a 5% solution of aquous sodium bicarbonate (100 mL)
2. 2
   其他the resulting bubbling
3. 3
   其他biphasic reaction mixture
4. 4
   workup.STIRRINGwas vigorously stirred at 0° C. for 15 m
5. 5
   萃取extracted with dichloromethane twice
6. 6
   洗涤The combined organic layers were washed with 1M hydrochloric acid
7. 7
   其他dried
8. 8
   浓缩concentrated by rotary evaporation
9. 9
   其他The product was purified by flash chromatography on silica gel (hexanes)

实验过程

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).

来源