Reaktion #92142

Reaktionsgleichung

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

N-[[4-bromo-3-(2,2,2-trifluoroethyl)phenyl]methylidene]hydroxylamine

→

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

Lösungsmittel

NaClO

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a 100-mL round-bottom flask, was placed
2. 2
   SonstigeThe reaction was then quenched by the addition of 10 mL of water
3. 3
   ExtraktionThe resulting solution was extracted with 3×20 mL of dichloromethane
4. 4
   WaschenThe resulting mixture was washed with 3×20 mL of brine
5. 5
   EinengenThe resulting mixture was concentrated under vacuum
6. 6
   SonstigeThis resulted in 600 mg (50%) of 3-[4-bromo-3-(2,2,2-trifluoroethyl)phenyl]-5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazole as yellow oil

Vorschrift

Into a 100-mL round-bottom flask, was placed 1-chloro-3-(trifluoromethyl)-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (680 mg, 2.48 mmol, 1.00 equiv), a solution of N-[[4-bromo-3-(2,2,2-trifluoroethyl)phenyl]methylidene]hydroxylamine (700 mg, 2.48 mmol, 1.10 equiv) in dichloromethane (20 mL), NaClO (10 mL). The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 10 mL of water. The resulting solution was extracted with 3×20 mL of dichloromethane and the organic layers combined. The resulting mixture was washed with 3×20 mL of brine. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:30-1:10). This resulted in 600 mg (50%) of 3-[4-bromo-3-(2,2,2-trifluoroethyl)phenyl]-5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazole as yellow oil.

Quelle