Sodium Iodide → HCID 19966029, Verbindung

HRID 977892Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 977892
[I-:1].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13]OS(C)(=O)=O)=[CH:9][C:8]=1[N+:19]([O-:21])=[O:20])([CH3:6])([CH3:5])[CH3:4]>CC(C)=O>[C:3]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][I:1])=[CH:9][C:8]=1[N+:19]([O-:21])=[O:20])([CH3:6])([CH3:5])[CH3:4]

Komponenten

4

Edukt 2

HCID 5238Sodium IodideHCID 19966051HCID 19966051, Verbindung

Produkt 1

HCID 19966029HCID 19966029, VerbindungAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

1.65 g (11 mmol) of sodium iodide were added to a solution of 2.00 g (6.96 mmol) of 2-t-butyl-5-(methanesulfonyloxymethyl)-1-nitrobenzene [prepared as described in step (i) above] in 40 ml of acetone, and the mixture was stirred at 50° C. for 20 minutes. At the end of this time, the reaction mixture was cooled to room temperature, and filtered. The precipitate was washed with ethyl acetate, and the combined filtrate and washings were concentrated by evaporation under reduced pressure. The concentrate was dissolved in ethyl acetate, and the resulting solution was washed with water, with an aqueous solution of sodium thiosulfate, and with a saturated aqueous solution of sodium chloride, in that order. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure, to give 2.18 g (yield 98%) of the title compound as crystals, melting at 98°-99° C. (after recrystallization from a mixture of methylene chloride, diethyl ether and hexane). Infrared Absorption Spectrum (KBr), νmax cm-1 : 1530, 1370, 1250, 1169, 1061, 886, 839, 807, 627.

Aufarbeitung

  1. temperatureAt the end of this time, the reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. washThe precipitate was washed with ethyl acetate
  4. concentrationthe combined filtrate and washings were concentrated by evaporation under reduced pressure
  5. dissolutionThe concentrate was dissolved in ethyl acetate
  6. washthe resulting solution was washed with water, with an aqueous solution of sodium thiosulfate
  7. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  8. customthe solvent was removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d1ce05062ad9436da4c47140d4945539
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05614550

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