Azobisisobutyronitrile → 2-[4-(Bromomethyl)-3-fluorophenyl]-1H-isoindole-1,3(2H)-dione

HRID 1861938

反応式

HRID 1861938 の反応式
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12]3=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]3[C:10]2=[O:19])[CH:5]=[CH:6][C:7]=1[CH3:8].[Br:20]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N:9]2[C:10](=[O:19])[C:11]3=[CH:18][CH:17]=[CH:16][CH:15]=[C:12]3[C:13]2=[O:14])=[CH:3][C:2]=1[F:1]

参加物

5

反応物 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 6833332-(3-fluoro-4-methylphenyl)-1H-isoindole-1,3(2H)-dione

生成物 1

HCID 186217392-[4-(Bromomethyl)-3-fluorophenyl]-1H-isoindole-1,3(2H)-dione収率 46.2%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

A mixture of the compound (1.0 g) obtained in Example 248, N-bromosuccinimide (698 mg), α,α′-azobis(isobutyronitrile) (catalytic amount) and carbon tetrachloride (20 ml) was heated under reflux for 16 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=8:2) to give 605 mg of the titled compound (yield, 46%).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 16 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=8:2)

出典と根拠

ORDレコード
ord-a27b827d9e374742a1868381b22c1f70
出典データセット
uspto-grants-2003_03
特許番号
US06534546B1

関連ノート

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