Trifluoroacetic acid → 4-Chloro-5-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone

HRID 21260Notes

Reaction equation

HRID 21260 reaction equation
[Cl:1][C:2]1[C:10]([O:11]COC)=[CH:9][C:8]([I:15])=[C:7]2[C:3]=1[CH:4](O)[N:5]([C:17]([CH3:25])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:18])[C:6]2=[O:16].FC(F)(F)C(O)=O.C([SiH](CC)CC)C.C(=O)([O-])O.[Na+]>[N+](C)([O-])=O.O>[Cl:1][C:2]1[C:10]([OH:11])=[CH:9][C:8]([I:15])=[C:7]2[C:3]=1[CH2:4][N:5]([C:17]([CH3:25])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:18])[C:6]2=[O:16]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 68492299HCID 68492299, compound

Product 1

HCID 684939844-Chloro-5-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinoneYield 108%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6375NitromethaneSolvent

Procedure

In a similar manner to Step 4 of Example 16, 4-chloro-5-methoxymethoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (100 mg, 0.21 mmol) was dissolved in nitromethane (4 mL), and the solution was treated with trifluoroacetic acid (0.097 mL, 1.26 mmol) and triethylsilane (0.200 mL, 1.25 mmol). The mixture was added with water and saturated aqueous sodium hydrogencarbonate solution 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 to obtain 4-chloro-5-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (97.0 mg, yield 98%).

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

Sources & evidence

ORD record
ord-1bb3b9cb8735410c8b91dde127e1ef07
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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