N-bromobutanimide → 1,2-Benzisoxazole, 6-bromo-3-(bromomethyl)-

HRID 1988871ノート

反応式

HRID 1988871 の反応式
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6]([CH3:9])=[N:7][O:8][C:4]=2[CH:3]=1.[Br:12]N1C(=O)CCC1=O.N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6]([CH2:9][Br:12])=[N:7][O:8][C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 67184N-bromobutanimideHCID 749781,1'-Azobis(cyclohexanecarbonitrile)HCID 124113226-Bromo-3-methyl-1,2-benzoxazole

生成物 1

HCID 586565221,2-Benzisoxazole, 6-bromo-3-(bromomethyl)-収率 37.8%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

A mixture of 6-bromo-3-methyl-1,2-benzisoxazole (675 mg), N-bromosuccinimide (642 mg) and 1,1′-azobis(cyclohexanecarbonitrile) (90 mg) in carbon tetrachloride (7 ml) was irradiated using a 300W lamp at reflux under nitrogen for 40 h. On cooling the precipitate was removed by filtration, the solvent was evaporated and the residue was purified by flash chromatography on a silica column (4 cm diam) eluting with a cyclohexane-ethyl acetate gradient (49:1 to 24:1) to give the title compound as a pale yellow solid (350 mg).

後処理

  1. customwas irradiated
  2. temperatureat reflux under nitrogen for 40 h
  3. temperatureOn cooling the precipitate
  4. customwas removed by filtration
  5. customthe solvent was evaporated
  6. customthe residue was purified by flash chromatography on a silica column (4 cm diam)
  7. washeluting with a cyclohexane-ethyl acetate

出典と根拠

ORDレコード
ord-fc207a8ba19d4c1bb10d308b9478302c
出典データセット
uspto-grants-2010_01
特許番号
US07642276B2

反応ノート

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