Triethylamine → Phenylphosphine

HRID 412839

Reaktionsgleichung

Reaktionsgleichung von HRID 412839
IC1C=CC=CC=1.C(N(CC)CC)C.[C:15]1(C)[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[P:21](C1C=CC=CC=1C)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1C.P>[Pd].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C(C)=CC=CC=1>[C:16]1([PH2:21])[CH:17]=[CH:18][CH:19]=[CH:20][CH:15]=1.[C:22]1([PH:21][C:16]2[CH:15]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 11575IodobenzeneHCID 24404PhosphineHCID 80271Tri-o-tolylphosphine

Produkt 2

HCID 12519PhenylphosphineAusbeute 9 %HCID 70017DiphenylphosphineAusbeute 7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 7237O-XyleneLösungsmittel2×

Versuchsvorschrift

A one liter xylene solution containing iodobenzene (375 g, 1.84 moles), triethylamine (150 g, 1.5 moles) and the palladium dimer (1:1 adduct of palladium(II) acetate and tri(o-tolyl)phosphine, 1.20 g, 1.2 mmole, 0.07 mole %) was charged to a one gallon autoclave under a nitrogen blanket. The solution was maintained at 500 psig phosphine pressure and 110° C., with stirring at 500 rpm, for 5 hours. At this time the autoclave was cooled to ambient temperature, vented and discharged as described above. Analysis of the xylene phase by GC/FID (with area percent integration) gave only monophenylphosphine (9%) and diphenylphosphine (7%), with no sign of triphenyl-phosphine, for a total conversion of iodobenzene of approximately 16%.

Quellen und Nachweise

ORD-Eintrag
ord-56768d8b3dc6459d9590b91c2a5eadbe
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06563005B1

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