Hydrochloric Acid → 6-(Trifluoromethyl)isobenzofuran-1(3H)-one

HRID 604039Notes

Reaction equation

HRID 604039 reaction equation
Br[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][OH:13].C(N(CC)CC)C.Cl.[C:22](OCC)(=[O:24])C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[F:9][C:8]([F:11])([F:10])[C:7]1[CH:2]=[C:3]2[C:4]([CH2:22][O:24][C:12]2=[O:13])=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 670872702-Bromo-3-(trifluoromethyl)benzyl alcohol

Product 1

HCID 110744416-(Trifluoromethyl)isobenzofuran-1(3H)-one

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6228DimethylformamideSolvent

Procedure

(2-Bromo-trifluoromethyl-phenyl)-methanol (5 g) is dissolved in N,N-dimethylformamide (45 ml) and thereto are added palladium acetate (440 mg), 1,1′-bis(diphenylphosphino)ferrocene (2.17 g) and triethylamine (2 (5 ml), and the mixture is stirred under carbon monooxide flow at room temperature for 5 minutes and at 90° C. for 1 day. The reaction solution is cooled to room temperature, and thereto are added a 1N-hydrochloric acid and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=4:1→3:2) to give 6-trifluoromethyl-3H-isobenzofuran-1-one (2.77 g). MS (m/z): 203 [M+H]+

Workup

  1. waitat 90° C. for 1 day
  2. temperatureThe reaction solution is cooled to room temperature
  3. customthe mixture is separated
  4. washthe organic layer is washed with a saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=4:1→3:2)

Sources & evidence

ORD record
ord-f24de1e9a6d44edcb530cb74d8d6b6f4
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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