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

HRID 527520Notes

Reaction equation

HRID 527520 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-f9283790676b454eab2e3e83a0ddffd1
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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