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

HRID 19537
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HRID 19537 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 23964Tungsten촉매
HCID 5943
Carbon Tetrachloride
용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-93b0980d393d482f97ea807b4febef77
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07745439B2

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