Iodine chloride → Tetramethyl m-iodophenyl-1-hydroxy-ethylidenebis(phosphonate)

HRID 1265949Notes

Reaction equation

HRID 1265949 reaction equation
C[Si](C)(C)[C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:23])([P:17](=[O:22])([O:20][CH3:21])[O:18][CH3:19])[P:11](=[O:16])([O:14][CH3:15])[O:12][CH3:13])[CH:6]=[CH:7][CH:8]=1.[I:26]Cl>C(O)(=O)C>[I:26][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:23])([P:17](=[O:22])([O:20][CH3:21])[O:18][CH3:19])[P:11](=[O:16])([O:14][CH3:15])[O:12][CH3:13])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 11144043Tetramethyl m-trimethylsilylphenyl-1-hydroxy-ethylidenebis(phosphonate)

Product 1

HCID 11134386Tetramethyl m-iodophenyl-1-hydroxy-ethylidenebis(phosphonate)Yield 81.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Tetramethyl m-trimethylsilylphenyl-1-hydroxy-ethylidenebis(phosphonate) (0.41 g, 1.0 mmol) was added to a solution of ICl (0.32 g, 2.0 mmol) in acetic acid (2 cm3) and the mixture was stirred for 5 h. The solvent was then evaporated and the residue was extracted with 1:1 hexane:Et2O (2×10 cm3). Remaining solvents were removed from the residue under reduced pressure affording the title compound (0.38 g, 81%) as an orange liquid.

Workup

  1. customThe solvent was then evaporated
  2. extractionthe residue was extracted with 1:1 hexane
  3. customRemaining solvents were removed from the residue under reduced pressure

Sources & evidence

ORD record
ord-e85cde087f0a43ea88a86f7441e45d63
Source dataset
uspto-grants-2003_04
Patent number
US06548042B2

Reaction notes

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