Water → 1H-Inden-1-one, 4-bromo-2,3-dihydro-5-(trifluoromethyl)-

HRID 2406509Notes

Reaction equation

HRID 2406509 reaction equation
[Br:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][C:14]([OH:16])=O.O>FC(F)(F)S(O)(=O)=O>[Br:1][C:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][CH:5]=[C:4]2[C:3]=1[CH2:12][CH2:13][C:14]2=[O:16]

Participants

4

Reactant 2

HCID 962WaterHCID 53808869Benzenepropanoic acid, 2-bromo-3-(trifluoromethyl)-

Product 1

HCID 867007731H-Inden-1-one, 4-bromo-2,3-dihydro-5-(trifluoromethyl)-

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

3-(2-Bromo-3-trifluoromethyl-phenyl)-propionic acid (3.25 g) in trifluoromethane-sulfonic acid (30 ml) is stirred at 75° C. for 2.5 h. After cooling to room temperature, the mixture is poured into water and the resulting mixture is extracted with ethyl acetate. The combined organic extract is washed with aqueous NaHCO3 solution, dried (Na2SO4), and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10→80:20) to afford the title compound. LC (method 5): tR=0.90 min.

Workup

  1. extractionthe resulting mixture is extracted with ethyl acetate
  2. extractionThe combined organic extract
  3. washis washed with aqueous NaHCO3 solution
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10→80:20)

Sources & evidence

ORD record
ord-03cd12b569d944b895e291befb69779e
Source dataset
uspto-grants-2014_08
Patent number
US08809376B2

Reaction notes

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