Tributylphosphine → Ferrocene-1,1'-bis-(diphenylphosphine)

HRID 1028914Notes

Reaction equation

HRID 1028914 reaction equation
[C:1]1(OP(O[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C-]2C=CC=C2)C=CC=C[CH:2]=1.[C-:21]1(P(O[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)OC2C=CC=CC=2)C=CC=[CH:22]1.[Fe+2:41].[CH2:42]([P:46]([CH2:51][CH2:52][CH2:53][CH3:54])[CH2:47][CH2:48][CH2:49][CH3:50])[CH2:43][CH2:44][CH3:45].[C:55](#N)C.[CH2:58]1COCC1>II>[C:35]1([P:46]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C-:51]2[CH:52]=[CH:53][CH:54]=[CH:55]2)[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1.[C-:51]1([P:46]([C:42]2[CH:22]=[CH:21][CH:45]=[CH:44][CH:43]=2)[C:47]2[CH:2]=[CH:1][CH:50]=[CH:49][CH:48]=2)[CH:58]=[CH:54][CH:53]=[CH:52]1.[Fe+2:41]

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 22177404Acetonitrile tetrahydrofuranHCID 178506418HCID 178506418, compound

Product 1

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Yield 94%

Reagents, catalysts & solvents 1

HCID 807IodineCatalyst

Procedure

100 mg (0.171 mmol) of 1,1′-Bis(diphenyloxyphosphino)ferrocene were treated with I2 4 mg (16 μmol) and tributylphosphine 170 μL (0.68 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 ethanol, the resulting crystals were filtered, washed and dried in vacuum, giving 89 mg (0.160 mmol, 94%) of 1,1′-Bis(diphenylphosphino)ferrocene (dppf).

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 ethanol
  8. filtrationthe resulting crystals were filtered
  9. washwashed
  10. customdried in vacuum

Sources & evidence

ORD record
ord-ebfca4431dd846daacbfbd844d5a65a7
Source dataset
uspto-grants-2014_05
Patent number
US08735629B2

Reaction notes

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