N-bromobutanimide → 6-Bromo-2,3-dihydro-1H-inden-5-amine

HRID 260677노트

반응식

HRID 260677 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2.[Br:11]N1C(=O)CCC1=O>CN(C)C=O>[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Br:11])[CH2:7][CH2:6][CH2:5]2

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 90496Indan-5-amine

생성물 1

HCID 224002746-Bromo-2,3-dihydro-1H-inden-5-amine수율 68.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

5-Aminoindan (3.0 g, 22.5 mmol) was dissolved in 10 ml of anhydrous dimethylformamide. A solution of N-bromosuccinimide (4.0 g, 22.5 mmol) in 10 ml anhydrous dimethylformamide was added, and the reaction mixture was stirred at room temperature for 1.5 hours. The reaction mixture was partitioned between ethyl acetate and water, and the separated organic layer washed twice with H2O, then with brine. Drying over Na2SO4 followed by filtration and evaporation of solvent gave a dark brown oil as the crude product. Purification by flash chromatography (50% EtOAc/hexane) provided 5-amino-6-bromoindan (3.26 g, 68% yield), a compound of Formula 2 where X is bromo, as a brown oil which crystallized into a brown solid.

후처리

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washthe separated organic layer washed twice with H2O
  3. dry with materialDrying over Na2SO4
  4. filtrationfollowed by filtration and evaporation of solvent
  5. customgave a dark brown oil as the crude product
  6. customPurification by flash chromatography (50% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-adc0e8320ebe4f82a38074a525e81765
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05530005

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