Water → 4-Chloro-5-methoxy-7-iodoisoindolinone

HRID 21246Notes

Reaction equation

HRID 21246 reaction equation
[Cl:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([I:13])=[C:7]2[C:3]=1[CH:4](O)[N:5](C(C)(C1C=CC=CC=1)C)[C:6]2=[O:14].FC(F)(F)C(O)=O.C([SiH](CC)CC)C.O>[N+](C)([O-])=O.CCCCCC.C(OCC)(=O)C>[Cl:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([I:13])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:14]

Participants

8

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 684892124-Chloro-5-methoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone

Product 1

HCID 684924484-Chloro-5-methoxy-7-iodoisoindolinoneYield 64.2%

Reagents, catalysts & solvents 3

HCID 6375NitromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a similar manner to Step 4 of Example 16, 4-chloro-5-methoxy-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (300 mg, 0.655 mmol) was dissolved in nitromethane (5 mL), and the solution was treated with trifluoroacetic acid (0.505 mL, 6.55 mmol) and triethylsilane (0.212 mL, 1.31 mmol), followed by stirring at room temperature for 24 hours. The reaction mixture was added with water, ethyl acetate and hexane. The precipitated solid was collected by filtration and washed with hexane and water, followed by drying under reduced pressure to obtain 4-chloro-5-methoxy-7-iodoisoindolinone (136 mg, yield 64%).

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with hexane and water
  3. customby drying under reduced pressure

Sources & evidence

ORD record
ord-dd693a902a3342af89c07ffd9aa57680
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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