Cesium carbonate → 3-Iodo-5-methanesulfonyl-phenol

HRID 418064

Reaktionsgleichung

Reaktionsgleichung von HRID 418064
C1C=CC(/C=N\O)=CC=1.[C:10](=[O:13])([O-])[O-].[Cs+].[Cs+].[I:16][C:17]1[CH:22]=C([N+]([O-])=O)[CH:20]=[C:19]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:18]=1>CN(C=O)C.CCOC(C)=O>[I:16][C:17]1[CH:22]=[C:10]([OH:13])[CH:20]=[C:19]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:18]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 5324470Syn-benzaldehyde oximeHCID 578630421-Iodo-3-(methanesulfonyl)-5-nitrobenzene

Produkt 1

HCID 578630243-Iodo-5-methanesulfonyl-phenolAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of syn-benzaldehyde oxime (3.71 g, 30.6 mmol) in DMF (80 mL) was added cesium carbonate (19.9 g, 61.3 mmol) and heated to 90° C. for 1-2 min before a solution of 1-iodo-3-methanesulfonyl-5-nitro-benzene (5.0 g, 15.3 mmol) in DMF (80 mL) was added. The resulting dark brown solution was stirred at 90° C. for 15 h. The reaction mixture was then cooled down and diluted with EtOAc and washed with 10% HCl. The organic phase was then washed again with brine. The combined organic extracts were dried over sodium sulfate and evaporated under reduced pressure to obtain a crude brown oil which was purified on ISCO column (330 g). The desired compound was eluted with 70% EtOAc-Hexanes. The desired fractions were combined and evaporated under reduced pressure to afford 2.5 g (55%) of 3-iodo-5-methanesulfonyl-phenol as an orange solid. HR-ES(+) m/e calcd for C7H7O3SI (M+H)+ 298.9234, found 298.9234.

Aufarbeitung

  1. additionwas added
  2. temperatureThe reaction mixture was then cooled down
  3. washwashed with 10% HCl
  4. washThe organic phase was then washed again with brine
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customto obtain a crude brown oil which
  8. customwas purified on ISCO column (330 g)
  9. washThe desired compound was eluted with 70% EtOAc-Hexanes
  10. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1cb235526fba460f86844677a2254a6e
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093253B2

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