Trifluoromethanesulfonic acid → 5-Trifluoromethylindane

HRID 907074Notes

Reaction equation

HRID 907074 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11](O)=O)[CH:6]=[CH:7][CH:8]=1.FC(F)(F)S(O)(=O)=O>O>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][CH:8]=1)[CH2:11][CH2:10][CH2:9]2

Participants

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 27776833-(3-Trifluoromethylphenyl)propanoic acid

Product 1

HCID 673889025-Trifluoromethylindane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To 3-(3-trifluoromethylphenyl)propionic acid was added trifluoromethanesulfonic acid at room temperature, followed by stirring at 60° C. for 3 hours. The reaction liquid was put into cold water, followed by extraction with a mixed solvent of ethyl acetate and THF. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1 to 5:1) to obtain 5-trifluoromethylindane (2.2 g) and a compound of Reference Example 11 (0.70 g) as colorless solids, respectively.

Workup

  1. customThe reaction liquid
  2. extractionfollowed by extraction with a mixed solvent of ethyl acetate and THF
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1 to 5:1)

Sources & evidence

ORD record
ord-3d177b1eb4cf4f759396b71bbd8d0087
Source dataset
uspto-grants-2011_09
Patent number
US08013018B2

Reaction notes

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