Azobisisobutyronitrile → 4-Bromomethylperfluorobiphenyl

HRID 1391859

반응식

HRID 1391859 반응식
[CH3:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([C:10]2[C:15]([F:16])=[C:14]([F:17])[C:13]([F:18])=[C:12]([F:19])[C:11]=2[F:20])=[C:4]([F:21])[C:3]=1[F:22].[Br:23]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:23][CH2:1][C:2]1[C:3]([F:22])=[C:4]([F:21])[C:5]([C:10]2[C:15]([F:16])=[C:14]([F:17])[C:13]([F:18])=[C:12]([F:19])[C:11]=2[F:20])=[C:6]([F:9])[C:7]=1[F:8]

참가 물질

5

반응물 3

HCID 6547Azobisisobutyronitrile3회HCID 67184N-bromobutanimide3회HCID 587828944-Methylperfluorobiphenyl

생성물 1

HCID 865911214-Bromomethylperfluorobiphenyl수율 60%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

A mixed solution of a mixture comprising the 4-methylperfluorobiphenyl mentioned above, an N-bromo succinic imide (NBS) (26.7 g, 150 mmol), AIBN (0.99 g, 6 mmol) and a carbon tetrachloride (100 mL) was subjected to heating under reflux for 1 week. During this process, the progress of the reaction was confirmed by TLC, and NBS and AIBN were added on a timely basis. Ultimately, 285 mmol NBS and 15 mmol AIBN were added to the solution. After the reaction was completed, the solution was cooled to room temperature, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate=100:1), and the 4-(bromomethyl)perfluorobiphenyl (7.36 g, 18 mmol, total yield from methyl lithium 60%) was isolated. 1H NMR (CDCl3, 300 MHz) δ 4.58 (s, 2H, CH2Br); 19F NMR (CDCl3, 282 MHz) δ−138.02 (dd, J=10.6, 19.8 Hz, 2F), −138.56 (dt, J=9.1, 20.3 Hz, 2F), −142.36 (dd, J=10.6, 19.8 Hz, 2F), −150.59 (t, J=20.3 Hz, 1F), −161.08 (dt, J=7.1, 20.3 Hz, 2F).

후처리

  1. temperatureto heating
  2. temperatureunder reflux for 1 week
  3. additionwere added on a timely basis
  4. customthe solvent was removed under reduced pressure
  5. customThe crude product was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate=100:1)

출처 및 근거

ORD 기록
ord-b08486eec6644c59a47106afcc06c722
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07339082B2

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