Water → 3-Bromo-6-(cyclopropylmethoxy)phenanthrene

HRID 549498Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 549498
[Br:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[CH:11][C:10]1[CH:9]=[CH:8][C:7]([OH:16])=[CH:6][C:5]2=1.Br[CH2:18][CH:19]1[CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O.[I-].[K+]>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[CH:12]=[CH:11][C:10]3[C:5]([C:4]=2[CH:3]=1)=[CH:6][C:7]([O:16][CH2:18][CH:19]1[CH2:21][CH2:20]1)=[CH:8][CH:9]=3

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 86614876HCID 86614876, Verbindung

Produkt 1

HCID 866148783-Bromo-6-(cyclopropylmethoxy)phenanthreneAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 4875Potassium IodideKatalysatorHCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 6-bromophenanthren-3-ol (0.823 g, 3.02 mmol) from Step 1 above, (bromomethyl)cyclopropane (0.5 mL, 5.4 mmol), potassium carbonate (2.5 g, 18 mmol) and potassium iodide (5 mg) in acetone (50 mL) was heated at reflux for 3 days. Water was then added and the reaction mixture extracted with ethyl acetate The organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The crude material was purified by flash chromatography on silica (100% hexanes) to provide 3-bromo-6-(cyclopropylmethoxy)phenanthrene (0.859 g, 87%).

Aufarbeitung

  1. temperatureat reflux for 3 days
  2. extractionthe reaction mixture extracted with ethyl acetate The organic layer
  3. washwas washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by flash chromatography on silica (100% hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-61a4e6dcf62b499583111a8784ac2a2f
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943649B2

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