Azobisisobutyronitrile → 4-Bromomethylperfluorobiphenyl

HRID 459435ノート

反応式

HRID 459435 の反応式
[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]

参加物

5

反応物 3

HCID 6547Azobisisobutyronitrile3 回HCID 67184N-bromobutanimide3 回HCID 587828944-Methylperfluorobiphenyl

生成物 1

HCID 865911214-Bromomethylperfluorobiphenyl収率 60%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4b0ac3c02c7743b1a278c08395d09e75
出典データセット
uspto-grants-2007_03
特許番号
US07193113B2

反応ノート

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