Potassium Iodide → HCID 86639415, compound

HRID 1690182Notes

Reaction equation

HRID 1690182 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]([C:12]1[CH:29]=[C:28]([CH2:30][CH2:31][CH3:32])[C:15]([O:16][C:17]2[CH:18]=[CH:19][C:20]([N+]([O-])=O)=[C:21]([CH:24]=2)[CH:22]=[O:23])=[C:14]([CH2:33][CH2:34][CH3:35])[CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5].C(=O)([O-])O.[Na+].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.N([O-])=O.[Na+].[I-:59].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCOCC1.O.[Fe].O.C(O)(=O)C>[I:59][C:20]1[CH:19]=[CH:18][C:17]([O:16][C:15]2[C:28]([CH2:30][CH2:31][CH3:32])=[CH:29][C:12]([C:3]([O:8][CH2:9][O:10][CH3:11])([C:4]([F:7])([F:6])[F:5])[C:2]([F:37])([F:36])[F:1])=[CH:13][C:14]=2[CH2:33][CH2:34][CH3:35])=[CH:24][C:21]=1[CH:22]=[O:23]

Participants

11

Reactant 6

HCID 4875Potassium IodideHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 23668193Sodium NitriteHCID 86639416HCID 86639416, compound

Product 1

HCID 86639415HCID 86639415, compoundYield 7%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of 5-(4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2,6-dipropylphenoxy)-2-nitrobenzaldehyde (100 mg, 0.186 mmol) in dioxane/water (2:1, 1.7 mL), iron powder (26 mg, 0.465 mmol) and acetic acid (290 μL) were added sequentially under ice-cold conditions, and the resultant mixture was stirred at room temperature overnight. After completion of the reaction, water and a saturated aqueous solution of sodium hydrogen carbonate were added under ice-cold conditions, and the resultant mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. A solution of the obtained crude product (98 mg) in acetonitrile (0.744 mL) was added with p-toluene sulfonic acid monohydrate (106 mg, 0.558 mmol), added with a mixed aqueous solution (water 100 μL) of sodium nitrite (26 mg, 0.372 mmol) and potassium iodide (77 mg, 0.465 mmol) under ice-cold conditions, and stirred at the same temperature for 5 minutes. Subsequently, the resultant mixture was 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 (2-iodo-5-(4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2,6-dipropylphenoxy) benzaldehyde (8.0 mg, yield 7.0%) was obtained as a yellow oil.

Workup

  1. extractionthe resultant mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customA solution of the obtained crude product (98 mg) in acetonitrile (0.744 mL)
  6. extractiona saturated aqueous solution of sodium hydrogen carbonate, extracted with ethyl acetate
  7. concentrationconcentrated in vacuo
  8. customThe obtained residue was purified

Sources & evidence

ORD record
ord-df607b597800438fbc650835ff2f83be
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

Loading…