Iodine → 3'-Iodo-5'-(trifluoromethyl)-2,2,2-trifluoroacetophenone

HRID 1880261Notes

Reaction equation

HRID 1880261 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[CH:6]=[CH:7][CH:8]=1.S(=O)(=O)(O)O.[I:22]I>>[I:22][C:7]1[CH:6]=[C:5]([C:9](=[O:14])[C:10]([F:11])([F:12])[F:13])[CH:4]=[C:3]([C:2]([F:15])([F:16])[F:1])[CH:8]=1

Participants

4

Reactant 3

HCID 807IodineHCID 1118Sulfuric AcidHCID 1365592,2,2-Trifluoro-3'-(trifluoromethyl)acetophenone

Product 1

HCID 871835433'-Iodo-5'-(trifluoromethyl)-2,2,2-trifluoroacetophenone

Procedure

To 2.42 g of 3′-trifluoromethyl-2,2,2-trifluoroacetophenone, 6 mL of 30% fuming sulfuric acid and 1.90 g of iodine were added and the resultant mixture was stirred at 50° C. for 5 hours. After the completion of the reaction, the reaction mixture was charged onto 10 g of ice and the resultant mixture was extracted with diethyl ether (20 mL×1). The organic phase was washed with 10 mL of a saturated sodium sulfite aqueous solution and then dehydrated and dried over saturated saline and anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure to obtain 2.56 g of the objective substance as a light yellow oily substance.

Workup

  1. customAfter the completion of the reaction
  2. extractionthe resultant mixture was extracted with diethyl ether (20 mL×1)
  3. washThe organic phase was washed with 10 mL of a saturated sodium sulfite aqueous solution
  4. dry with materialdried over saturated saline and anhydrous sodium sulfate in this order
  5. distillationthe solvent was distilled off under reduced pressure
  6. customto obtain 2.56 g of the objective substance as a light yellow oily substance

Sources & evidence

ORD record
ord-a55df0a93fce4170843e572f19117ef8
Source dataset
uspto-grants-2012_11
Patent number
US08318757B2

Reaction notes

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