Peracetic Acid → 4-Iodobenzaldehyde
Reaction equation
[Na].[I-:2].C([O-])(=O)C.[NH4+].C(OO)(=O)C.C([Sn](CCCC)(CCCC)[C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=1)CCC>O.CO.C(#N)C>[I:2][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Procedure
To 5.2 μL sodium [123I] iodide (138.1 MBq) was added, ammonium acetate buffer (100 μL, pH 4, 0.2M), sodium [127I] iodide (51 μL, 10 mM solution in 0.01M sodium hydroxide, 5.1×10−7 moles), peracetic acid (11 μL, 50 mM solution, 5.5×10−7 moles) and 4-tributylstannyl benzaldehyde (100 μL, 200 μg, 2 mg/mL solution in acetonitrile, 5.06×10−7 moles). An additional 50 μL acetonitrile was added to aid solubility of the 4-tributylstannyl benzaldehyde, and the reaction mixture allowed to incubate at room temperature for approximately 20 minutes prior to HPLC analysis, which showed [123I]-4-iodobenzaldehyde (tR˜8 minutes, system A, Example 2) with an RCP of >90%. To the reaction mixture was added 1 mL acetonitrile and 10 mL water and the resulting solution loaded onto a tC-18 light cartridge (pre-treated with 2.5 mL methanol and 5 mL water). [123I]-4-iodobenzaldehyde was eluted with 0.5 mL 1:1 t-butanol:water in 48% yield (non-decay corrected).
Workup
- wash[123I]-4-iodobenzaldehyde was eluted with 0.5 mL 1:1 t-butanol
Sources & evidence
- ORD record
- ord-c6222524bfa94921bf1e9f9cbd6c4295
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08894971B2
Reaction notes
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