Potassium Carbonate → HCID 19067682, compound

HRID 1957473Notes

Reaction equation

HRID 1957473 reaction equation
[OH:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:18][C:19]1[C:24]([Cl:25])=[CH:23][C:22]([N+:26]([O-:28])=[O:27])=[C:21](F)[CH:20]=1>CS(C)=O>[Cl:25][C:24]1[C:19]([Cl:18])=[CH:20][C:21]([O:1][C:2]2[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=2)=[C:22]([N+:26]([O-:28])=[O:27])[CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5339511,2-Dichloro-4-fluoro-5-nitrobenzeneHCID 178481859HCID 178481859, compound

Product 1

HCID 19067682HCID 19067682, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-Hydroxy-1-methyl-3-trifluoromethylpyrazole (7.0 g, 40 mmol) and powdered potassium carbonate (11.4 g, 80 mmol) were stirred together in dimethylsulfoxide (40 ml) for 30 minutes. 4,5-Dichloro-2-fluoronitrobenzene (7.9 g, 50 mmol) was added and the mixture stirred at room temperature for 18 h. The mixture was partitioned between diethyl ether and water, the ethereal extract washed with water and brine, dried over magnesium sulfate, filtered and the filtrate evaporated. The residue was further purified by flash column chromatography over silica gel, to give the desired product (5.9 g) as a light yellow solid, m.p. 99°-100° C.

Workup

  1. customThe mixture was partitioned between diethyl ether and water
  2. extractionthe ethereal extract
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate evaporated
  7. customThe residue was further purified by flash column chromatography over silica gel

Sources & evidence

ORD record
ord-7d8d2f018bc64ba985e24d843ac97d1d
Source dataset
uspto-grants-1998_07
Patent number
US05786302

Reaction notes

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