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

HRID 527514
Notes
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Reaction equation

HRID 527514 reaction equation
[CH3:1][C:2]1[C:6]2=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=[C:5]2[O:4][N:3]=1.F[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][C:2]1[C:6]2[C:7]([O:11][C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 1354299403-Methyl-1,2-benzoxazol-4-ol2×

Product 1

HCID 679604203-Methyl-4-[(4-nitrophenyl)oxy]-1,2-benzisoxazoleYield 40.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

3-methyl-1,2-benzisoxazol-4-ol (Intermediate 10, 137 mg) was stirred with 1-fluoro-4-nitrobenzene (130 mg, 0.92 mmol) in DMF (3.0 ml) with potassium carbonate (381 mg, 2.8 mmol). The reaction mixture was heated at 110° C. for 1 hour under microwave irradiation After removal of the volatiles, the residue was purified by silica gel chromatography eluting with CyHex/EtOAc (100%/0% to 0%/100%) to afford the title compound (100 mg).

Workup

  1. customAfter removal of the volatiles
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with CyHex/EtOAc (100%/0% to 0%/100%)

Sources & evidence

ORD record
ord-1b63a13f91a048239be3477651799cf1
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09346790B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes