HCID 86654468、化合物 → 3-[4-Bromo-3-(2,2,2-trifluoroethyl)phenyl]-5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazole

HRID 63864ノート

反応式

HRID 63864 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([C:10](F)(F)F)=C)[CH:5]=[C:4]([C:14]([F:17])([F:16])[F:15])[CH:3]=1.[Br:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]=[N:26][OH:27])=[CH:21][C:20]=1[CH2:28][C:29]([F:32])([F:31])[F:30]>ClCCl.[O-]Cl.[Na+]>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH2:10][CH:8]([C:6]3[CH:5]=[C:4]([C:14]([F:15])([F:16])[F:17])[CH:3]=[C:2]([Cl:1])[CH:7]=3)[O:27][N:26]=2)=[CH:21][C:20]=1[CH2:28][C:29]([F:30])([F:31])[F:32]

参加物

5

反応物 2

HCID 86654468HCID 86654468、化合物HCID 131737209HCID 131737209、化合物

生成物 1

HCID 1180469173-[4-Bromo-3-(2,2,2-trifluoroethyl)phenyl]-5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazole

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 23665760Sodium Hypochlorite溶媒

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.

後処理

  1. customInto a 100-mL round-bottom flask, was placed
  2. customThe reaction was then quenched by the addition of 10 mL of water
  3. extractionThe resulting solution was extracted with 3×20 mL of dichloromethane
  4. washThe resulting mixture was washed with 3×20 mL of brine
  5. concentrationThe resulting mixture was concentrated under vacuum
  6. customThis 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

出典と根拠

ORDレコード
ord-60918547806c4f6bb226db00c2d23777
出典データセット
uspto-grants-2016_09
特許番号
US09447084B2

反応ノート

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