Sulfuryl chloride → 4-Chloro-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole

HRID 644848Notes

Reaction equation

HRID 644848 reaction equation
S(Cl)([Cl:4])(=O)=O.[Cl:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([Cl:17])[C:8]=1[O:18][C:19]1[CH:23]=[C:22]([CH3:24])[NH:21][N:20]=1>C(O)(=O)C>[Cl:4][C:23]1[C:19]([O:18][C:8]2[C:7]([Cl:6])=[CH:12][C:11]([C:13]([F:16])([F:14])[F:15])=[CH:10][C:9]=2[Cl:17])=[N:20][NH:21][C:22]=1[CH3:24]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 178623603-(2,6-Dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole

Product 1

HCID 178624724-Chloro-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazoleYield 55%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sulfuryl chloride (0.48 g, 3.6 mmol) was added to a solution of 3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole (0.93 g, 3.0 mmol) in acetic acid (10 ml), and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, the reaction mixture was poured into ice water and extracted with ethyl acetate (10 ml×3). An organic layer was washed with water, dried over anhydrous magnesium sulfate and filtered to remove a desiccant, and the solvent was distilled off from the filtrate under reduced pressure. The resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/10), to give a white solid of 4-chloro-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole (0.57 g, yield: 55.0%). mp: 156-158° C.; 1H-NMR (CDCl3, TMS, ppm): δ 2.28 (s, 3H), 7.65 (s, 2H), 8.75-9.15 (br s, 1H).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (10 ml×3)
  3. washAn organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customto remove a desiccant, and the solvent
  7. distillationwas distilled off from the filtrate under reduced pressure
  8. customThe resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/10)

Sources & evidence

ORD record
ord-e81dc4946be24f0880d6d77419d98e2f
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

Loading…