تفاعل #2075718

معادلة التفاعل

Bis(2-methoxyethyl)aminosulfur trifluoride

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

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title compound

المردود 65.8%

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

المردود 65.8%

المذيبات

water

dichloromethane

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر