Water → 4-Chloro-7-iodoisoindolinone

HRID 21008Notes

Reaction equation

HRID 21008 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[C:7]2[C:3]=1[CH:4](O)[N:5](C(C)(C1C=CC=CC=1)C)[C:6]2=[O:12].FC(F)(F)C(O)=O.C([SiH](CC)CC)C.O>[N+](C)([O-])=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 684876174-Chloro-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone

Product 1

HCID 684927354-Chloro-7-iodoisoindolinoneYield 99.5%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

4-Chloro-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (6.94 g, 16.2 mmol) was dissolved in nitromethane (280 mL), and the solution was added with trifluoroacetic acid (17.7 mL, 230 mmol) and triethylsilane (7.35 mL, 46.1 mmol), followed by stirring at room temperature for 23 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by slurry using diisopropyl ether to obtain 4-chloro-7-iodoisoindolinone (4.73 g, yield 99%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by slurry

Sources & evidence

ORD record
ord-28e4bbeac1234af7ae468230af2c7cb8
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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