Azobisisobutyronitrile → 6-bromomethyl-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

HRID 19535

반응식

HRID 19535 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:22])[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]([CH3:21])[CH:9]=2)=[O:5])[CH3:2].[Br:23]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl.[W]>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:22])[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]([CH2:21][Br:23])[CH:9]=2)=[O:5])[CH3:2]

참가 물질

6

반응물 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 686992925-Methyl-3-oxo-1-phenylindene-2-carboxylic acid ethyl ester

생성물 1

HCID 686975466-bromomethyl-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester수율 36.7%

시약·촉매·용매 2

HCID 23964Tungsten촉매HCID 5943Carbon Tetrachloride용매

실험 절차

6-Methyl-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (3 g, 10.3 mmol) obtained in Step 4 was dissolved in carbon tetrachloride, and N-bromosuccinimide (2 g, 11.4 mmol) and 2,2′-azobisisobutyronitrile (500 mg, 3.09 mmol) were added thereto. The mixture was refluxed for 3 hrs under the irradiation of a 375 W tungsten lamp. Upon the completion of the reaction, the resulting 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 to obtain 1.4 g of the titled compound (yield: 36.7%) in oil state.

후처리

  1. customUpon the completion of the reaction
  2. washthe resulting 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

출처 및 근거

ORD 기록
ord-98d8b10c0bda4888ab506e69cf8a6076
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745439B2

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