反応 #2075718

反応方程式

Bis(2-methoxyethyl)aminosulfur trifluoride

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

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title compound

収率 65.8%

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

収率 65.8%

溶媒

water

dichloromethane

反応条件

後処理

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

実験手順

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).

出典