Reacción #92150

Ecuación de reacción

(E)-N-[(4-bromonaphthalen-1-yl)methylidene]hydroxylamine

1-chloro-3-(trifluoromethyl)-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

chlorosylsodium

→

3-(4-bromonaphthalen-1-yl)-5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroInto a 250-mL round-bottom flask purged
2. 2
   Temperaturamaintained with an inert atmosphere of nitrogen
3. 3
   ExtracciónThe aqueous layer was extracted with 3×20 mL of dichloromethane
4. 4
   Lavadowashed with 3×40 mL of brine
5. 5
   SecadoThe organic phase was dried over anhydrous sodium sulfate
6. 6
   Concentraciónconcentrated under vacuum
7. 7
   Lavadowashed with ethyl acetate/petroleum ether (1/10-1/5)
8. 8
   OtroThis resulted in 7.1 g (75%) of 3-(4-bromonaphthalen-1-yl)-5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole as a off-white solid

Procedimiento

Into a 250-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed dichloromethane (100 mL), (E)-N-[(4-bromonaphthalen-1-yl)methylidene]hydroxylamine (4.5 g, 17.99 mmol, 1.00 equiv), 1-chloro-3-(trifluoromethyl)-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (4.9 g, 17.84 mmol, 1.00 equiv), chlorosylsodium (30 mL). The resulting solution was stirred overnight at room temperature. The aqueous layer was extracted with 3×20 mL of dichloromethane and the organic layers combined and washed with 3×40 mL of brine. The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and washed with ethyl acetate/petroleum ether (1/10-1/5). This resulted in 7.1 g (75%) of 3-(4-bromonaphthalen-1-yl)-5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole as a off-white solid.

Fuente