Azobisisobutyronitrile → 2-Bromo-3-phenyl-6-(3-phenylpropoxy)indene-1-one

HRID 19537

反応式

HRID 19537 の反応式
[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>C(Cl)(Cl)(Cl)Cl.[W]>[Br:27][C:8]1[C:9](=[O:26])[C:10]2[C:15]([C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:11]=2

参加物

6

反応物 3

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

生成物 1

HCID 686950762-Bromo-3-phenyl-6-(3-phenylpropoxy)indene-1-one収率 60%

試薬・触媒・溶媒 2

HCID 23964Tungsten触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

3-Phenyl-6-(3-phenyl-propoxy)-indene-1-one (200 mg, 0.586 mmol) obtained in Step 1 was dissolved in carbon tetrachloride, and N-bromosuccinimide (313 mg, 1.75 mmol) and 2,2′-azobisisobutyronitrile (9.7 mg) were added thereto. The mixture was refluxed for 1 hr 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:hexane=1:5) to obtain 147 mg of the titled compound (yield: 60%) as a red solid.

後処理

  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:hexane=1:5)

出典と根拠

ORDレコード
ord-93b0980d393d482f97ea807b4febef77
出典データセット
uspto-grants-2010_06
特許番号
US07745439B2

関連ノート

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