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

HRID 471459Notes

Reaction equation

HRID 471459 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

Conditions

Temperature
85 °C

Procedure

3-(2-Bromo-3-trifluoromethyl-phenyl)-propionic acid (3.0 g, 10.1 mmol) is suspended in trifluoromethanesulfonic acid (30 mL)) under argon and heated at 85° C. for 4 hours. The mixture is added dropwise to iced water and then extracted with ethyl acetate. The organic extract is washed with saturated sodium bicarbonate solution, dried and concentrated under vacuum. The residue is purified by flash chromatography (Eluent 0-5% EtOAc in cyclohexane) to give the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washis washed with saturated sodium bicarbonate solution
  4. customdried
  5. concentrationconcentrated under vacuum
  6. customThe residue is purified by flash chromatography (Eluent 0-5% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-962ec0282eea4bd1935c15bb6dfbed29
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

Loading…