Azobisisobutyronitrile → 1-(Bromomethyl)-4-fluoro-2-iodobenzene

HRID 1711084노트

반응식

HRID 1711084 반응식
[Br:1]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C.[F:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[C:24]([I:29])[CH:23]=1>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:28][C:25]1[CH:26]=[CH:27][C:22]([F:21])=[CH:23][C:24]=1[I:29]

참가 물질

5

반응물 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 832204-Fluoro-2-iodotoluene

생성물 1

HCID 128060541-(Bromomethyl)-4-fluoro-2-iodobenzene수율 58%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

N-Bromosuccinimide (0.61 g, 3.4 mmol) and VAZO (0.10 g, 0.41 mmol) were added to a solution of 4-fluoro-2-iodotoluene (0.75 g, 3.2 mmol) in carbon tetrachloride (45 mL). The resulting suspension was stirred and heated under reflux for 18 hours. It was then cooled and filtered, the solid was rinsed with carbon tetrachloride (5 mL), and the combined filtrates were concentrated under reduced pressure. The residue was purified by flash column chromatography (eluting with hexanes) to provide 322 (0.58 g, 58% yield). 1H NMR (400 MHz, CDCl3) δ (ppm): 7.51 (dd, J=8.0, 2.5 Hz, 1H); 7.38 (dd, J=8.4, 5.7 Hz, 1H); 7.00 (dt, J=8.2, 2.7 Hz, 1H); 4.54 (s, 2H).

후처리

  1. temperatureheated
  2. temperatureunder reflux for 18 hours
  3. temperatureIt was then cooled
  4. filtrationfiltered
  5. washthe solid was rinsed with carbon tetrachloride (5 mL)
  6. concentrationthe combined filtrates were concentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography (eluting with hexanes)

출처 및 근거

ORD 기록
ord-2330a2641b644ba894609481f9315db2
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790729B2

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