Sodium Iodide → 5-Iodomethyl-1-methyl-3-(4-trifluoromethoxy-phenyl)-1H-pyrazole

HRID 915470Notes

Reaction equation

HRID 915470 reaction equation
Cl[CH2:2][C:3]1[N:7]([CH3:8])[N:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)[CH:4]=1.[I-:20].[Na+].COC(C)(C)C>CC(C)=O>[I:20][CH2:2][C:3]1[N:7]([CH3:8])[N:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 15413tert-Butyl methyl etherHCID 674021555-chloromethyl-1-methyl-3-(4-trifluoromethoxy-phenyl)-1H-pyrazole

Product 1

HCID 674028105-Iodomethyl-1-methyl-3-(4-trifluoromethoxy-phenyl)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 5-chloromethyl-1-methyl-3-(4-trifluoromethoxy-phenyl)-1H-pyrazole (3.2 g, 11 mmol; example 19 a]) and sodium iodide (8.25 g, 55 mmol) in acetone (56 ml) was heated under reflux conditions for 30 min. Tert butyl methyl ether was added, the solid was filtered off and the filtrate was brought to dryness under reduced pressure. The residue was dissolved in tert butyl methyl ether, washed with ice water/brine 1/1 and the aqueous layer was extracted two times with tert butyl methyl ether. The combined extracts were washed with aqueous sodium thiosulfate solution and brine and dried over sodium sulfate. The solvent was removed under reduced pressure to give the title compound as yellow oil which was used in the next step without further purification.

Workup

  1. filtrationthe solid was filtered off
  2. dissolutionThe residue was dissolved in tert butyl methyl ether
  3. washwashed with ice water/brine 1/1
  4. extractionthe aqueous layer was extracted two times with tert butyl methyl ether
  5. washThe combined extracts were washed with aqueous sodium thiosulfate solution and brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-dcdacbeec97744d7b60bd052640eb04c
Source dataset
uspto-grants-2007_09
Patent number
US07265149B2

Reaction notes

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