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

HRID 19546

반응식

HRID 19546 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 23964Tungsten촉매HCID 6344Dichloromethane용매

실험 절차

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.

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/n-hexane=1/20→1/9)

출처 및 근거

ORD 기록
ord-dbb54efd464f4ac8818e337f503f8cdb
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745439B2

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