Potassium Iodide → HCID 86639420, compound

HRID 1690185Notes

Reaction equation

HRID 1690185 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:24][CH2:25][O:26][CH3:27])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=2[CH2:28][CH2:29][CH3:30])[CH:5]=[CH:4][C:3]=1N.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.N([O-])=O.[Na+].[I-:48].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[F:18][C:16]([F:17])([F:19])[C:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][C:6]2[CH:5]=[CH:4][C:3]([I:48])=[C:2]([CH3:1])[CH:7]=2)=[C:10]([CH2:28][CH2:29][CH3:30])[CH:11]=1)([O:24][CH2:25][O:26][CH3:27])[C:20]([F:22])([F:21])[F:23]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 24477Sodium ThiosulfateHCID 521998p-Toluenesulfonic acid monohydrateHCID 23668193Sodium NitriteHCID 86639418HCID 86639418, compound

Product 1

HCID 86639420HCID 86639420, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  1. stirringstirred at room temperature overnight
  2. extractiona saturated aqueous solution of sodium hydrogen carbonate, extracted with ethyl acetate
  3. concentrationconcentrated in vacuo
  4. customThe obtained residue was purified

Sources & evidence

ORD record
ord-328e30056e004935a4af4de3922663b4
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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