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Iodine → (Diethylamino)-bis(2,4-dimethylphenyl)phosphine

HRID 459425
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 459425
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH3:9].[Mg].II.[N:13]([P:18](Cl)Cl)([CH2:16][CH3:17])[CH2:14][CH3:15]>CCOCC.C1COCC1>[CH2:14]([N:13]([P:18]([C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH3:9])[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH3:9])[CH2:16][CH3:17])[CH3:15]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 807IodineHCID 68503Benzene, 1-bromo-2,4-dimethyl-HCID 2733289Dichloro(diethylamino)phosphineHCID 5462224Magnesium

Produkt 1

HCID 23064861(Diethylamino)-bis(2,4-dimethylphenyl)phosphine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl Ether
Lösungsmittel
2×
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 2.92 ml (21.61 mmol) of 4-bromo-1,3-dimethylbenzene in 3 ml of Et2O were added at 0° C. to a suspension of 0.5 g (20.56 mmol) of magnesium turnings in 7 ml of THF and 7 ml of Et2O and also a crystal of iodine. The mixture was heated to room temperature, stirred further overnight and slowly added dropwise at 0° C. to a solution of 1.5 ml (10.31 mmol) of Et2NPCl2 in 8 ml of THF. The mixture was heated to 5–10° C., stirred for a further 2 hours and the solvent was subsequently removed under reduced pressure. After adding 60 ml of hexane, the mixture was filtered through Celite under argon and the solvent was subsequently removed under reduced pressure. Yield: 1.37 g (59% of theory). 1H NMR (400 MHz, CDCl3) δ, 6.9 (m, 6H), 3.03 (m, 4H, CH2), 2.20 (s, 12H, CH3), 0.81 (t, 3J=7.0 Hz, 6H, CH3) 31P NMR (161.9 MHz, CDCl3) δ, 47.8.

Aufarbeitung

  1. temperatureThe mixture was heated to 5–10° C.
  2. stirringstirred for a further 2 hours
  3. customthe solvent was subsequently removed under reduced pressure
  4. additionAfter adding 60 ml of hexane
  5. filtrationthe mixture was filtered through Celite under argon
  6. customthe solvent was subsequently removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9f93fb23994e4224abf00c391f2229eb
Quelldatensatz
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07193092B2

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