p-Fluoronitrobenzene → 3,6-Dimethyl-4-[(4-nitrophenyl)oxy]-1,2-benzisoxazole

HRID 527520ノート

反応式

HRID 527520 の反応式
[CH3:1][C:2]1[C:6]2=[C:7]([OH:12])[CH:8]=[C:9]([CH3:11])[CH:10]=[C:5]2[O:4][N:3]=1.F[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][C:2]1[C:6]2[C:7]([O:12][C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=3)=[CH:8][C:9]([CH3:11])=[CH:10][C:5]=2[O:4][N:3]=1

参加物

5

反応物 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 1363786503,6-Dimethyl-1,2-benzisoxazol-4-ol2 回

生成物 1

HCID 679598393,6-Dimethyl-4-[(4-nitrophenyl)oxy]-1,2-benzisoxazole収率 34.7%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

3,6-dimethyl-1,2-benzisoxazol-4-ol (Intermediate 19, 345 mg) was dissolved in acetonitrile (10.0 ml) and then 1-fluoro-4-nitrobenzene (298 mg, 2.11 mmol) and potassium carbonate (877 mg, 6.34 mmol) were added. The reaction mixture was stirred and heated at reflux overnight. After removal of the volatiles, the residue was purified by silica gel chromatography eluting with a gradient cHex/EtOAc from 100/0 to 50/50 to afford the title compound (208 mg).

後処理

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customAfter removal of the volatiles
  4. customthe residue was purified by silica gel chromatography
  5. washeluting with a gradient cHex/EtOAc from 100/0 to 50/50

出典と根拠

ORDレコード
ord-f9283790676b454eab2e3e83a0ddffd1
出典データセット
uspto-grants-2016_05
特許番号
US09346790B2

反応ノート

読み込み中…