Trifluoroacetic acid → 4-Hydroxy-5-methyl-7-iodoisoindolinone

HRID 21277Notes

Reaction equation

HRID 21277 reaction equation
COC[O:4][C:5]1[C:13]([CH3:14])=[CH:12][C:11]([I:15])=[C:10]2[C:6]=1[CH:7](O)[N:8](C(C)(C1C=CC=CC=1)C)[C:9]2=[O:16].FC(F)(F)C(O)=O.C([SiH](CC)CC)C.C(=O)([O-])O.[Na+]>[N+](C)([O-])=O.C(OCC)(=O)C>[OH:4][C:5]1[C:13]([CH3:14])=[CH:12][C:11]([I:15])=[C:10]2[C:6]=1[CH2:7][NH:8][C:9]2=[O:16]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 68490123HCID 68490123, compound

Product 1

HCID 684874154-Hydroxy-5-methyl-7-iodoisoindolinoneYield 52.1%

Reagents, catalysts & solvents 2

HCID 6375NitromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a similar manner to Step. 4 of Example 16, 4-methoxymethoxy-5-methyl-3-hydroxy-7-iodo-2-(1-methyl-1-phenylethyl)isoindolinone (500 mg, 1.07 mmol) was dissolved in nitromethane (20 mL), and the solution was treated with trifluoroacetic acid (0.742 mL, 9.63 mmol) and triethylsilane (1.54 mL, 9.64 mmol). The reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution and ethyl acetate. The precipitated solid was collected by filtration and washed with water, followed by drying under reduced pressure to obtain 4-hydroxy-5-methyl-7-iodoisoindolinone (161 mg, yield 52%).

Workup

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

Sources & evidence

ORD record
ord-1e82547495c24af0a018eb52b19dc314
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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