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

HRID 1861938

반응식

HRID 1861938 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-a27b827d9e374742a1868381b22c1f70
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06534546B1

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