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

HRID 1970225Notes

Reaction equation

HRID 1970225 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-147f3fdfe601418b9017d1b6a52be34e
Source dataset
uspto-grants-2013_04
Patent number
US08426647B2

Reaction notes

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