Iodine → 1-Ethyl-2-iodo-4-(trifluoromethyl)benzene

HRID 924672Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 924672
S(=O)(=O)(O)O.I([O-])(=O)(=O)=O.[Na+].[I:12]I.[CH2:14]([C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1)[CH3:15].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(O)(=O)C>[I:12][C:17]1[CH:18]=[C:19]([C:22]([F:23])([F:24])[F:25])[CH:20]=[CH:21][C:16]=1[CH2:14][CH3:15]

Komponenten

7

Edukt 5

HCID 807IodineHCID 1118Sulfuric AcidHCID 656671Sodium PyrosulfiteHCID 53246974-EthylbenzotrifluorideHCID 23667635Sodium periodate

Produkt 1

HCID 709807481-Ethyl-2-iodo-4-(trifluoromethyl)benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Sulfuric acid (96%, 1.9 mL) was added drop wise to a solution of sodium periodate (3.73 g, 17.4 mmol) and iodine (2.95 g, 11.6 mmol) in a mixture acetic acid (8.45 mL) acetic anhydride (4.23 mL) at 0° C., followed by the drop wise addition of 1-ethyl-4-(trifluoromethyl)benzene (2.0 g, 11.6 mmol). The reaction mixture was let warming up to room temperature while stirring for a period of 24 h. A solution of sodium metabisulfite (10%) was added to quench the remaining iodine and successively, sodium hydroxide (35%) was added to reach pH=7. The aqueous layer was extracted with DCM (3×50 mL) and the combined organic layers were dried over sodium sulfate. Once the solvent was removed, the crude was used without further purification in the next step.

Aufarbeitung

  1. customto quench the remaining iodine
  2. additionsuccessively, sodium hydroxide (35%) was added
  3. extractionThe aqueous layer was extracted with DCM (3×50 mL)
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. customOnce the solvent was removed
  6. customthe crude was used without further purification in the next step

Quellen und Nachweise

ORD-Eintrag
ord-9f2fc634e6f5487780f4a0da3f49a8f7
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09283224B2

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