[CH2:1]([S-:4])[CH2:2][CH3:3].[Na+].[Br:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9](F)[CH:8]=1.O>CN(C=O)C>[Br:6][C:7]1[CH:8]=[C:9]([S:4][CH2:1][CH2:2][CH3:3])[CH:10]=[C:11]([F:13])[CH:12]=1Dissolve 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.
Wird geladen…
