p-Fluoronitrobenzene → 4-fluoro-1-(4-nitrophenyl)-1H-pyrazole

HRID 537430Notes

Reaction equation

HRID 537430 reaction equation
[F:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].F[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1>C(#N)C>[F:1][C:2]1[CH:3]=[N:4][N:5]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 1419924-fluoro-1H-pyrazole

Product 1

HCID 237295164-fluoro-1-(4-nitrophenyl)-1H-pyrazoleYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-fluoro-1H-pyrazole (250 mg, 2.90 mmol) and potassium carbonate (803 mg, 5.81 mmol) in acetonitrile (3 mL) was added 4-fluoronitrobenzene (430 mg, 3.05 mmol). The resulting mixture was stirred at 70° C. for 2 hours. The reaction was then filtered and concentrated. Purification by column chromatography gave 4-fluoro-1-(4-nitrophenyl)-1H-pyrazole (400 mg, 67%). 1H NMR (400 MHz, CDCl3, δ): 8.34 (d, 2H), 7.91 (d, 1H), 7.81 (d, 2H), 7.67 (d, 1H).

Workup

  1. filtrationThe reaction was then filtered
  2. concentrationconcentrated
  3. customPurification by column chromatography

Sources & evidence

ORD record
ord-c8b069a3a51f4541b7c0c221c857a615
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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