Pyrazole → 1-(2,6-Dichloro-4-nitrophenyl)-pyrazole

HRID 1709694

Reaction equation

HRID 1709694 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[H-].[Na+].[Cl:8][C:9]1[CH:10]=[C:11]([N+:17]([O-:19])=[O:18])[CH:12]=[C:13]([Cl:16])[C:14]=1F>CN(C=O)C>[Cl:8][C:9]1[CH:10]=[C:11]([N+:17]([O-:19])=[O:18])[CH:12]=[C:13]([Cl:16])[C:14]=1[N:1]1[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 24758Sodium hydrideHCID 765541,3-Dichloro-2-fluoro-5-nitrobenzene

Product 1

HCID 230365521-(2,6-Dichloro-4-nitrophenyl)-pyrazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Pyrazole (1.43 g, 21,0 mmol) in 3 ml of DMF is added dropwise at RT to a suspension of sodium hydride (50%; 1.0 g, 21.0 mmol) in 10 ml of DMF. The mixture is stirred at RT for 30 min., after which it is added dropwise at 5° over a period of 30 min. to a solution of 3,5-dichloro-4-fluoronitrobenzene (3.0 g, 15.0 mmol) in 20 ml of DMF. After reaction is complete, the reaction mixture is quenched with water and extracted with ethyl acetate. The combined organic layers are washed with water and with brine and dried to give a yellow solid, 1-(2,6-dichloro-4-nitrophenyl)-pyrazole.

Workup

  1. customAfter reaction
  2. customthe reaction mixture is quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers are washed with water and with brine
  5. customdried

Sources & evidence

ORD record
ord-e9cf5a8757d7446da8ef330c5a36ec4c
Source dataset
uspto-grants-1990_08
Patent number
US04950678

Linked notes

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