Azobisisobutyronitrile → 1-bromo-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

HRID 19546

Reaktionsgleichung

Reaktionsgleichung von HRID 19546
[CH2:1]([O:3][C:4]([C:6]1[CH2:7][C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2].[Br:23]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>ClCCl.[W]>[CH2:1]([O:3][C:4]([C:6]1[CH:7]([Br:23])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2]

Komponenten

6

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 118451126-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

Produkt 1

HCID 686984701-bromo-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl esterAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23964TungstenKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

6-Methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (1.5 g, 5.10 mmol) prepared in Preparation Example 1 was dissolved in dichloromethane (80 mL), and N-bromosuccinimide (1.09 g, 6.12 mmol) and 2,2′-azobisisobutyronitrile (0.08 mg, 0.51 mmol) were added thereto. The mixture was stirred for 2 hrs at RT under the irradiation of a 375 W tungsten lamp. Upon the completion of the reaction, the mixture washed with saturated saline and extracted with dichloromethane. The organic layer was separated, dried over anhydrous MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography (ethyl acetate/n-hexane=1/20→1/9) to obtain 1.4 g of the titled compound (yield: 74%) as a yellow solid.

Aufarbeitung

  1. customUpon the completion of the reaction
  2. washthe mixture washed with saturated saline
  3. extractionextracted with dichloromethane
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated under a reduced pressure
  7. customThe resulting residue was purified by flash chromatography (ethyl acetate/n-hexane=1/20→1/9)

Quellen und Nachweise

ORD-Eintrag
ord-dbb54efd464f4ac8818e337f503f8cdb
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745439B2

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