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

HRID 17894

반응식

HRID 17894 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-carboxylate ethyl ester (3 g, 10.3 mmol) 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. Then, the mixture was refluxed for 3 hours under a 375 W tungsten lamp. After the reaction is completed, the organic layer was extracted with dichloromethane/saturated sodium chloride, dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by column chromatography to obtain 6-bromomethyl-1-oxo-3-phenyl-1H-indene-2-carboxylate ethyl ester (1.4 g, yield 36.7%) as yellow oil.

후처리

  1. extractionthe organic layer was extracted with dichloromethane/saturated sodium chloride
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customthe resulting residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-3886912e1cf84b7b8345cc647357f727
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741323B2

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