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

HRID 527520노트

반응식

HRID 527520 반응식
[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

참가 물질

5

반응물 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 1363786503,6-Dimethyl-1,2-benzisoxazol-4-ol2회

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f9283790676b454eab2e3e83a0ddffd1
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346790B2

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