Iodine → Triphenylphosphine

HRID 1028916Notes

Reaction equation

HRID 1028916 reaction equation
[C:1]1([P:7](=O)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.II.C(P(CCCC)CCCC)CCC>C(#N)C.C1COCC1>[C:14]1([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 807IodineHCID 13097Triphenylphosphine OxideHCID 13831Tributylphosphine

Product 1

HCID 11776TriphenylphosphineYield 93%

Reagents, catalysts & solvents 1

HCID 22177404Acetonitrile tetrahydrofuranSolvent

Procedure

100 mg (0.359 mmol) of triphenylphosphine oxide were treated with 9 mg I2 (35 μmol) and tributylphosphine 180 μL (0.72 mmol) in acetonitrile/THF (1:1 v/v) 1 mL. The mixture was stirred at room temperature for 10 minutes under nitrogen atmosphere before it was quenched with H2O (100 μL). The reaction mixture was diluted with ethyl acetate (10 mL) and was washed with portions of sat. NaHCO3 (3×5 mL). The organic fraction was dried with Na2SO4, filtered and the solvent evaporated under vacuum. The resulting residue was recrystallized from methanol, the resulting crystals were filtered, washed and dried in vacuum, giving 88 mg (0.334 mmol, 93%) of triphenylphosphine.

Workup

  1. customwas quenched with H2O (100 μL)
  2. additionThe reaction mixture was diluted with ethyl acetate (10 mL)
  3. washwas washed with portions of sat. NaHCO3 (3×5 mL)
  4. dry with materialThe organic fraction was dried with Na2SO4
  5. filtrationfiltered
  6. customthe solvent evaporated under vacuum
  7. customThe resulting residue was recrystallized from methanol
  8. filtrationthe resulting crystals were filtered
  9. washwashed
  10. customdried in vacuum

Sources & evidence

ORD record
ord-dde5214534014f7cbb0fa0d9a9b733d7
Source dataset
uspto-grants-2014_05
Patent number
US08735629B2

Reaction notes

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