反応 #92142

反応方程式

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

溶媒

NaClO

dichloromethane

反応条件

後処理

1. 1
   その他Into a 100-mL round-bottom flask, was placed
2. 2
   その他The reaction was then quenched by the addition of 10 mL of water
3. 3
   抽出The resulting solution was extracted with 3×20 mL of dichloromethane
4. 4
   洗浄The resulting mixture was washed with 3×20 mL of brine
5. 5
   濃縮The resulting mixture was concentrated under vacuum
6. 6
   その他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

実験手順

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.

出典