N-bromobutanimide → 2-Bromo-3-ethoxycyclopent-2-enone

HRID 28733

Reaktionsgleichung

Reaktionsgleichung von HRID 28733
[CH2:1]([O:3][C:4]1[CH2:8][CH2:7][C:6](=[O:9])[CH:5]=1)[CH3:2].C1C(=O)N([Br:17])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:17][C:5]1[C:6](=[O:9])[CH2:7][CH2:8][C:4]=1[O:3][CH2:1][CH3:2]

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 897773-Ethoxycyclopent-2-en-1-one

Produkt 1

HCID 107269112-Bromo-3-ethoxycyclopent-2-enone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

3-Ethoxy-cyclopent-2-enone (Intermediate NINE1) (commercially available from Aldrich) (10.0 g, 77.6 mmol) in carbon tetrachloride (15 mL) at 0° C. was treated with NBS (15.3 g, ˜85 mmol) added portion-wise over 30 m. After 1 h at 0° C. the mixture was partitioned between CH2Cl2 and saturated NaHCO3. The aqueous layer was extracted with CH2Cl2. The pooled organic layers were washed with H2O (2×) and dried over MgSO4. The mixture was filtered and evaporated to dryness. The solid was recrystallized from pentane:ether to give 13.3 g of 2-bromo-3-ethoxy-cyclopent-2-enone (Intermediate NINE2).

Aufarbeitung

  1. additionadded portion-wise over 30 m
  2. customAfter 1 h at 0° C. the mixture was partitioned between CH2Cl2 and saturated NaHCO3
  3. extractionThe aqueous layer was extracted with CH2Cl2
  4. washThe pooled organic layers were washed with H2O (2×)
  5. dry with materialdried over MgSO4
  6. filtrationThe mixture was filtered
  7. customevaporated to dryness
  8. customThe solid was recrystallized from pentane

Quellen und Nachweise

ORD-Eintrag
ord-9b61efe99d314c19ac1f0bac070f5faa
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419994B2

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