Trifluoroacetic acid → 4-fluoro-2,3-dihydro-1H-isoindol-1-one

HRID 877234Notes

Reaction equation

HRID 877234 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4](O)[NH:5][C:6]2=[O:11].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:11]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 668996124-fluoro-3-hydroxy-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 220646804-fluoro-2,3-dihydro-1H-isoindol-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.05 g (about 24.2 mmol) of 4-fluoro-3-hydroxy-2,3-dihydro-1H-isoindol-1-one were initially charged in 10 ml of dichloromethane, 22.4 ml (290.8 mmol) of trifluoroacetic acid and 7.7 ml (48.5 mmol) of triethylsilane were added and the mixture was stirred at RT overnight. The reaction mixture was then concentrated and the residue was dissolved in dichloromethane and washed with sodium bicarbonate solution. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 3:1 to 1:1). This gave 890 mg (24.2% of theory) of the target compound.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with sodium bicarbonate solution
  4. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 3:1 to 1:1)

Sources & evidence

ORD record
ord-c14164ba6d434abdb9d050b4df5652f5
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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