Phosphorus tribromide → 3-(3-bromopropyl)-1H-indole

HRID 1031488

Reaktionsgleichung

Reaktionsgleichung von HRID 1031488
P(Br)(Br)[Br:2].O[CH2:6][CH2:7][CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1>CCOCC>[Br:2][CH2:6][CH2:7][CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1

Komponenten

4

Edukt 2

HCID 24614Phosphorus tribromideHCID 77115Indole-3-propanol

Produkt 1

HCID 100371923-(3-bromopropyl)-1H-indoleAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

Phosphorus tribromide (17.4 g) in Et2O (30 mL) was added dropwise to a Et20 solution (100 mL) containing 3-(3-hydroxypropyl)indole (VI; 7.5 g) at 0° C. with stirring and under N2 atmosphere. After the addition was complete, the reaction was allowed to warm to 23° C. and continuously stirred for 16 h. At the end of this time, the reaction was cooled to 0° C. and ice (ca. 25 mL) added portionwise and stirred an additional 2 h. The organic phase was separated from the aqueous phase and the aqueous layer extracted with Et2O. The combined organic phases were washed with sat. NaCl solution, dried with MgSO4. filtered and concentrated under reduced pressure to afford 3-(3-bromopropyl)indole (V; 1.51 g; 15%).

Aufarbeitung

  1. additionAfter the addition
  2. stirringcontinuously stirred for 16 h
  3. temperatureAt the end of this time, the reaction was cooled to 0° C.
  4. stirringstirred an additional 2 h
  5. customThe organic phase was separated from the aqueous phase
  6. extractionthe aqueous layer extracted with Et2O
  7. washThe combined organic phases were washed with sat. NaCl solution
  8. dry with materialdried with MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e348e412d7de42618b1f9aad72b72f1d
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04954502

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