Azobisisobutyronitrile → (6-Bromo-3-bromomethyl-benzofuran-2-yl)(2,4-dichlorophenyl)-methanone

HRID 29242

반응식

HRID 29242 반응식
[Br:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6]([CH3:19])=[C:7]([C:9]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=3[Cl:18])=[O:10])[O:8][C:4]=2[CH:3]=1.N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:34]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6]([CH2:19][Br:34])=[C:7]([C:9]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=3[Cl:18])=[O:10])[O:8][C:4]=2[CH:3]=1

참가 물질

5

반응물 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 59788907(6-Bromo-3-methyl-benzofuran-2-yl)(2,4-dichloro-phenyl)methanone

생성물 1

HCID 59788888(6-Bromo-3-bromomethyl-benzofuran-2-yl)(2,4-dichlorophenyl)-methanone수율 68.5%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

To a stirred solution of (6-Bromo-3-methyl-benzofuran-2-yl)-(2,4-dichloro-phenyl)-methanone (4.0 g, 10.4 mmol) in carbon tetrachloride (40 mL) was added 2,2′-azobisisobutyronitrile (AIBN) (171 mg, 1.04 mmol) and N-bromosuccinimide (1.95 g, 10.9 mmol). The reaction mixture was heated at reflux for 6 h, and upon cooling to rt, the resulting precipitate was removed by filtration and the filtrate was concentrated. The crude residue was purified by column chromatography (10% ethyl acetate in hexanes) to afford the desired product (3.30 g, 65% yield) as a white solid. Rf=0.68 (10% EtOAc in hexanes). 1H-NMR (acetone): δ 7.98(d, 1H), 7.91 (s, 1H), 7.74 (m, 2H), 7.64 (td, 2H), 5.16 (s, 2H).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 6 h
  3. customthe resulting precipitate was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customThe crude residue was purified by column chromatography (10% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-20639e06089d4185a6519fa1fc357550
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420066B2

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