Iodine → HCID 57428844, Verbindung

HRID 507619Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 507619
II.[PH2](O)=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:16]2[S:17][CH:18]=[CH:19][N:20]=2)(O)[CH3:14])=[CH:9][CH:8]=1.[OH-].[Na+]>C(O)(=O)C>[F:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([C:16]2[S:17][CH:18]=[CH:19][N:20]=2)[CH3:14])=[CH:9][CH:8]=1

Komponenten

6

Edukt 4

HCID 807IodineHCID 14798Sodium HydroxideHCID 4124402Phosphinic AcidHCID 57428843HCID 57428843, Verbindung

Produkt 1

HCID 57428844HCID 57428844, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of iodine (856 mg, 3.37 mmol), hypophosphorous acid (3.152 mL, 20.22 mmol) and acetic acid (40 mL) was heated to 60° C. until the reaction mixture became clear. 1-(4-fluorophenyl)-1-(thiazol-2-yl)ethanol (1.05 g, 5.07 mmol) was added to the solution and the reaction mixture was heated to 80° C. overnight. After cooling to rt, the reaction mixture was neutralized with concentrated sodium hydroxide and the crude product was extracted with chloroform, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography with 0-40% ethyl acetate in hexane to afford the title compound as an oily brown residue (351 mg, 50% yield). MS (M+H)+ 208.

Aufarbeitung

  1. temperaturethe reaction mixture was heated to 80° C. overnight
  2. temperatureAfter cooling to rt
  3. extractionthe crude product was extracted with chloroform
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography with 0-40% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-99a43512c9f24fa7854078f0ffafd8db
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786132B2

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