Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | Sodium Thiosulfate | HCID 24477 | — |
| Reactant | p-Toluenesulfonic acid monohydrate | HCID 521998 | — |
| Reactant | Sodium Nitrite | HCID 23668193 | — |
| Reactant | HCID 86639418 | HCID 86639418 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 86639420 | HCID 86639420 | 67% |
Reaction Steps
To a solution of 2-methyl-4-[2-propyl-4-(2,2,2-trifluoro-1-methoxymethoxy-1-trifluoromethyl-ethyl)-phenoxy]-phenylamine (271 mg, 0.600 mmol) in acetonitrile (3.0 mL), p-toluene sulfonic acid monohydrate (342 mg, 1.80 mmol) was added. The resultant mixture was added with a mixed aqueous solution (water 400 μL) of sodium nitrite (83 mg, 1.20 mmol) and potassium iodide (249 mg, 1.50 mmol) at 10° C., stirred at the same temperature for 10 minutes, and then stirred at room temperature overnight. The reaction solution was added with an aqueous solution of sodium thiosulfate and a saturated aqueous solution of sodium hydrogen carbonate, extracted with ethyl acetate, and concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate), and 4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-1-(4-iodo-3-methylphenoxy)-2-propylbenzene (226 mg, yield 67%) was obtained as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08153634B2 |
|---|
| Source dataset | uspto-grants-2012_04 |
|---|
| ORD ID | ord-328e30056e004935a4af4de3922663b4 |
|---|
| Source note | uspto-grants-2012_04 |
|---|