Sodium Iodide → 4-Fluorophenyl-1-iodopropane

HRID 1063467

Reaktionsgleichung

Reaktionsgleichung von HRID 1063467
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[CH2:9][CH3:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[I-:24].[Na+]>ClCCl.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([I:24])[CH2:9][CH3:10])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1024701-(4-Fluorophenyl)propan-1-ol

Produkt 1

HCID 222798134-Fluorophenyl-1-iodopropaneAusbeute 86,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The obtained 4-fluorophenylpropan-1-ol (4.83 g, 31.3 mmol) was dissolved in dichloromethane (50 ml), and triethylamine (6.55 ml, 47.0 mmol) and methanesulfonyl chloride (2.91 ml, 37.6 mmol) were added thereto in the ice bath followed by stirring under a nitrogen atmosphere for 30 minutes. The reaction mixture was diluted with dichloromethane (50 ml), and washed with 10% hydrochloric acid and subsequently with a saturated aqueous sodium chloride solution, and then dried over magnesium sulfate. The solvent was evaporated in vacuo, and the residue was dissolved in acetone (100 ml), and then sodium iodide (9.39 g, 62.6 mmol) was added thereto followed by stirring under a nitrogen atmosphere for 2 hours at 50° C. The reaction mixture was diluted with ethyl acetate (250 ml), and washed with 10% aqueous sodium thiosulfate solution and subsequently with a saturated aqueous sodium chloride solution, and then dried over magnesium sulfate. The solvent was evaporated in vacuo, and the residue was purified by flash chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=5:1-2:1) to afford 4-fluorophenyl-1-iodopropane (7.12 g, 86% yield) as a yellow oil.

Aufarbeitung

  1. washwashed with 10% hydrochloric acid and subsequently with a saturated aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo
  4. dissolutionthe residue was dissolved in acetone (100 ml)
  5. stirringby stirring under a nitrogen atmosphere for 2 hours at 50° C
  6. washwashed with 10% aqueous sodium thiosulfate solution and subsequently with a saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated in vacuo
  9. customthe residue was purified by flash chromatography on a silica gel column (elution solvent; hexane:ethyl acetate=5:1-2:1)

Quellen und Nachweise

ORD-Eintrag
ord-0087b843a3aa4980b64c97507ae26190
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06964976B2

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