Реакция #2075718

Уравнение реакции

Bis(2-methoxyethyl)aminosulfur trifluoride

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

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title compound

Выход 65.8%

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

Выход 65.8%

Растворители

water

dichloromethane

Условия реакции

Обработка

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

Методика

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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