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

HRID 2259619ノート

反応式

HRID 2259619 の反応式
[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

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 90496Indan-5-amine

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b69d7d2917b34a0aad5519eb2153ab5e
出典データセット
uspto-grants-1995_12
特許番号
US05475003

反応ノート

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