Iodine → Tris(4-chlorophenyl)phosphine

HRID 1970226

Reaktionsgleichung

Reaktionsgleichung von HRID 1970226
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([P:8](=O)([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.II.C(P(CCCC)CCCC)CCC>C(#N)C.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([P:8]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 807IodineHCID 13831TributylphosphineHCID 94943Tris(4-chlorophenyl)phosphine oxide

Produkt 1

HCID 70874Tris(4-chlorophenyl)phosphineAusbeute 99,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22177404Acetonitrile tetrahydrofuranLösungsmittel

Versuchsvorschrift

100 mg (0.262 mmol) of tris(4-chlorophenyl)phosphineoxide were treated with 6 mg I2 (26 μmol) and tributylphosphine 130 μL (0.52 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 (2 mL), the resulting crystals were filtered, washed and dried in vacuum, giving 95 mg (0.260 mmol, 99%) of tris(4-chlorophenyl)phosphine.

Aufarbeitung

  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 (2 mL)
  8. filtrationthe resulting crystals were filtered
  9. washwashed
  10. customdried in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-00a605984e804a1ab587252b68759a2c
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426647B2

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