반응 #48704

반응 방정식

sodium propanethiolate

1-bromo-3,5-difluorobenzene

water

→

1-bromo-3-fluoro-5-propylsulfanylbenzene

수율 90.0%

용매

DMF

반응 조건

후처리

1. 1
   온도warm to −15° C.
2. 2
   추출extract into hexanes (3×500 mL)
3. 3
   세척Wash the resulting organic solution with saturated aqueous sodium chloride (100 mL)
4. 4
   건조dry (magnesium sulfate)
5. 5
   여과filter
6. 6
   농축concentrate
7. 7
   여과Filter through a plug of silica gel
8. 8
   세척wash with 10:90 ethyl acetate
9. 9
   농축hexanes and concentrate

실험 절차

Dissolve sodium propanethiolate (7.5 g) in DMF (250 mL) at ambient temperature, then chill to −30° C. and add 1-bromo-3,5-difluorobenzene (8.35 mL). After 1 hour, warm to −15° C., and stir for an additional 3 hours. Pour into water (2 L) and extract into hexanes (3×500 mL). Wash the resulting organic solution with saturated aqueous sodium chloride (100 mL), dry (magnesium sulfate), filter and concentrate. Filter through a plug of silica gel, wash with 10:90 ethyl acetate:hexanes and concentrate to give 1-bromo-3-fluoro-5-propylsulfanylbenzene (16.2 g, 90%). The title compound is prepared essentially as described in Preparation 343.

출처