Triphenylphosphine dibromide → (4-Bromo-butyl)-cyclopentane

HRID 1004646Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1004646
[CH:1]1([CH2:6][CH2:7][CH2:8][CH2:9]O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:11]P(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(#N)C>[Br:11][CH2:9][CH2:8][CH2:7][CH2:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 70579Triphenylphosphine dibromideHCID 217976434-Cyclopentylbutan-1-ol

Produkt 1

HCID 22471771(4-Bromo-butyl)-cyclopentaneAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 4-cyclopentyl-butan-1-ol (3.1 g, 22 mmol) in acetonitrile (200 mL) was treated with dibromotriphenylphosphorane (10.1 g, 23.9 mmol). The reaction was stirred for two hours and quenched with water (10 mL). The reaction was diluted with dichloromethane (300 mL) and washed with water (3×100 mL). The organic phase was dried (MgSO4), filtered, and concentrated to yield an oil. The product was passed through a pad of silica to yield (4-bromo-butyl)-cyclopentane as a colorless oil (3.37 g, 76%). 1H NMR (CDCl3, 300 MHz) δ 3.42 (t, 7.0 Hz, 2 H), 1.9-1.7 (m, 4 H), 1.6-1.3 (m, 9 H), 1.07 (m, 2 H).

Aufarbeitung

  1. customquenched with water (10 mL)
  2. additionThe reaction was diluted with dichloromethane (300 mL)
  3. washwashed with water (3×100 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield an oil

Quellen und Nachweise

ORD-Eintrag
ord-63974033f3584ad7ab7a7ccdab11a245
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06051586

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