ChemicalBook CAS DataBase List 1,1'-Bis(diphenylphosphino)ferrocene

1,1'-Bis(diphenylphosphino)ferrocene synthesis

4synthesis methods

Product Name:1,1'-Bis(diphenylphosphino)ferrocene
CAS Number:12150-46-8
Molecular formula:C34H28FeP210*
Molecular Weight:554.38

Ferrocene, 1,1'-bis(diphenoxyphosphino)-

405164-68-3

12150-46-8

The general procedure for the synthesis of 1,1'-bis(diphenylphosphino)ferrocene (dppf) from the compound (CAS: 405164-68-3) is as follows: Example 4: 100 mg (0.171 mmol) of 1,1'-bis(diphenoxyphosphino)ferrocene was reacted with 4 mg (16 μmol) of I? and 170 μL (0.68 mmol) of tributylphosphine in 1 mL of acetonitrile/THF (1:1, v/v) mixed solvent. The reaction mixture was stirred at room temperature for 10 min under nitrogen protection, followed by quenching the reaction with 100 μL of H?O. The reaction was then quenched with 10 mL of ethyl acetate. The reaction mixture was diluted with 10 mL of ethyl acetate and washed three times (5 mL each) with saturated aqueous NaHCO?solution. The organic phase was dried with Na?SO?, filtered and concentrated under reduced pressure. The resulting residue was recrystallized with ethanol, the crystals were collected by filtration, washed and dried under vacuum to give 89 mg (0.160 mmol, 94% yield) of 1,1'-bis(diphenylphosphino)ferrocene (dppf).

405164-68-3
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12150-46-8
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Yield:12150-46-8 94%

Reaction Conditions:

with tributylphosphine;iodine in tetrahydrofuran;acetonitrile at 20; for 0.166667 h;Inert atmosphere;

Steps:

4

EXAMPLE 4100 mg (0.171 mmol) of l,l'-Bis(diphenyloxyphosphino)ferrocene were treated with I₂ 4 mg (16 μιηο) and tributylphosphine 170 μ_^ (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 H₂0 (100 μ). The reaction mixture was diluted with ethyl acetate (lOmL) and was washed with portions of sat. NaHC0₃ (3x5 mL). The organic fraction was dried with Na₂S0₄, 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 Ι,Γ- Bis(diphenylphosphino)ferrocene (dppf).

References:

WO2011/123037,2011,A1 Location in patent:Page/Page column 23