Sodium Chloride → 2-Bromo-3-phenyl-6-(3-phenylpropoxy)indane-1-one

HRID 17888

Reaktionsgleichung

Reaktionsgleichung von HRID 17888
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:13][CH:14]=3)[C:9](=[O:26])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:27]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.[Cl-].[Na+]>C(Cl)(Cl)(Cl)Cl.[W]>[Br:27][CH:8]1[CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:15]2[C:10](=[CH:11][C:12]([O:16][CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:13][CH:14]=2)[C:9]1=[O:26]

Komponenten

7

Edukt 4

HCID 5234Sodium ChlorideHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 686947433-Phenyl-6-(3-phenylpropoxy)indene-1-one

Produkt 1

HCID 686986112-Bromo-3-phenyl-6-(3-phenylpropoxy)indane-1-oneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23964TungstenKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

3-Phenyl-6-(3-phenylpropoxy)indene-1-one (200 mg, 0.586 mmol) was dissolved in carbon tetrachloride, and N-bromosuccinimide (313 mg, 1.75 mmol) and 2,2′-azobisisobutyronitrile (9.7 mg) were added thereto. Then, the mixture was refluxed for 1 hour under a 375 W tungsten lamp. After the reaction was completed, saturated sodium chloride was added thereto and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by column chromatography (ethyl acetate:hexane=1:5) to obtain title compound (147 mg, yield 60%) as a red solid.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customthe resulting residue was purified by column chromatography (ethyl acetate:hexane=1:5)

Quellen und Nachweise

ORD-Eintrag
ord-ed396cf9a44d4f77bc2069f108568801
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741323B2

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