Phosphorus tribromide → 1-(3-Bromopropyl)-4-methoxybenzene

HRID 363444

Reaktionsgleichung

Reaktionsgleichung von HRID 363444
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11]O)=[CH:5][CH:4]=1.P(Br)(Br)[Br:14]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][Br:14])=[CH:5][CH:4]=1

Komponenten

3

Edukt 2

HCID 24614Phosphorus tribromideHCID 794063-(4-Methoxyphenyl)-1-propanol

Produkt 1

HCID 127769961-(3-Bromopropyl)-4-methoxybenzeneAusbeute 61,1 %

Versuchsvorschrift

To a solution of 3-(p-methoxyphenyl)-1-propanol (16.6 g; 0.1 mol) in 250 mL of tolune, cooled to 0° C., was added dropwise 26 mL of phosphorus tribromide (0.27 mol). Following completion of the addition the reaction was stirred at room temperature for 1 hour, then refluxed for an additional hour. The reaction was cooled and poured onto ice, the layers were separated, and the organic phase washed with saturated sodium bicarbonate (3×) and brine (3×). The crude material obtained upon drying and evaporation of the solvent was chromatographed, eluting with 10%, EtOAc/hexane, to obtain 14 g (61%) of 3-(p-methoxyphenyl)-1-propylbromide.

Aufarbeitung

  1. additioncompletion of the addition the reaction
  2. temperaturerefluxed for an additional hour
  3. temperatureThe reaction was cooled
  4. additionpoured onto ice
  5. customthe layers were separated
  6. washthe organic phase washed with saturated sodium bicarbonate (3×) and brine (3×)
  7. customThe crude material obtained
  8. customupon drying
  9. customevaporation of the solvent
  10. customwas chromatographed
  11. washeluting with 10%, EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-27845d3556614a0a81e759015d137572
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05874449

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