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

HRID 924672Notes

Reaction equation

HRID 924672 reaction equation
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]

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9f2fc634e6f5487780f4a0da3f49a8f7
Source dataset
uspto-grants-2016_03
Patent number
US09283224B2

Reaction notes

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