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

HRID 551341Notes

Reaction equation

HRID 551341 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)=[O:4].S(=O)(=O)(O)O.[I:22]I>>[F:1][C:2]([F:15])([F:16])[C:3]([C:5]1[CH:6]=[C:7]([C:11]([F:12])([F:13])[F:14])[CH:8]=[C:9]([I:22])[CH:10]=1)=[O:4]

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-trifluoroacetophenoneYield 92.9%

Conditions

Temperature
50 °C

Procedure

A mixture of 2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethanone (2.42 g), 30% fuming sulfuric acid (6.0 mL) and iodine (1.90 g) was stirred at 50° C. for 5 hours. After the completion of the reaction, the mixture was poured into ice-water (10 g) and extracted with diethyl ether (20 mL×1). The organic layer was washed with saturated aqueous sodium sulfite solution (10 mL×1) and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to provide the title compound as a pale yellow oil (2.56 g).

Workup

  1. customAfter the completion of the reaction
  2. extractionextracted with diethyl ether (20 mL×1)
  3. washThe organic layer was washed with saturated aqueous sodium sulfite solution (10 mL×1) and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b52f9ae2b18f45c79f4dd56b80847ab3
Source dataset
uspto-grants-2011_05
Patent number
US07947715B2

Reaction notes

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