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Azobisisobutyronitrile → 4'-(Bromomethyl)-2-chloro-1,1'-biphenyl

HRID 2298140
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HRID 2298140 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])=[CH:4][CH:3]=1.C1C(=O)N([Br:22])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Br:22][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])=[CH:6][CH:7]=1
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참가 물질

6

반응물 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 123227902-Chloro-4'-methyl-1,1'-biphenyl

생성물 1

HCID 222468324'-(Bromomethyl)-2-chloro-1,1'-biphenyl수율 61.3%

시약·촉매·용매 2

HCID 5943Carbon Tetrachloride용매HCID 6344Dichloromethane
용매

실험 절차

A mixture of 4′-methyl-2-chloro-biphenyl (1.08 g, 5.33 mmol), NBS (1.14 g, 6.40 mmol) and AIBN (175 mg, 1.06 mmol) in CCl4 (37 mL) was heated at reflux for 3 h. The reaction mixture was diluted with CH2Cl2 and the organic solution was washed sequentially with aqueous saturated NaHCO3 (2×), water (1×), and brine (1×). The organic solution was dried over MgSO4, filtered, and concentrated in vacuo. The product was purified by flash chromatography (hexanes to 5% EtOAc/hexanes) to afford the title compound (920 mg). 1H NMR (CDCl3 400 MHz) δ 7.63-7.25 (m, 8H), 4.56 (s, 2H).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. washthe organic solution was washed sequentially with aqueous saturated NaHCO3 (2×), water (1×), and brine (1×)
  4. dry with materialThe organic solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by flash chromatography (hexanes to 5% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-8032acaa3c5f4cfd82d34009c5859fca
출처 데이터셋
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06492412B2

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