Phosphorus tribromide → (2E,6E)-1-bromo-3,7,11-trimethyldodeca-2,6,10-triene

HRID 327898

Reaktionsgleichung

Reaktionsgleichung von HRID 327898
O[CH2:2]/[CH:3]=[C:4](/[CH2:6][CH2:7]/[CH:8]=[C:9](/[CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])\[CH3:10])\[CH3:5].P(Br)(Br)[Br:18]>CCOCC>[CH3:5]/[C:4](/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:10])/[CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])=[CH:3]\[CH2:2][Br:18]

Komponenten

4

Edukt 2

HCID 24614Phosphorus tribromideHCID 445070Farnesol

Produkt 1

HCID 5366048(2E,6E)-1-bromo-3,7,11-trimethyldodeca-2,6,10-trieneAusbeute 215,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A solution of 1.00 g (4.5 mmol) of (E,E)-farnesol (Aldrich, further purified by flash chromatography) in 10 ml of distilled ether at 0° C. under argon in the dark was treated dropwise with a solution of 195 μL (2.05 mmol, 0.45 eq.) of PBr3 in 2 ml of ether. The resultant mixture was stirred at 0° C. for one hour, then quenched with water and separated. The organic phase was washed with 5 ml of H2O, 5 ml of saturated NaHCO3, and 5 ml of brine, dried over Na2SO4 and evaporated to give 1.26 g (98%) of crude bromide as a clear oil. TLC Silica (2:8 ethyl acetate:Hexane) Rf=0.69.

Aufarbeitung

  1. customquenched with water
  2. customseparated
  3. washThe organic phase was washed with 5 ml of H2O, 5 ml of saturated NaHCO3, and 5 ml of brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f6ed432f5a184febb9b77f8e8178b2f1
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05273969

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