Azobisisobutyronitrile → 4-Bromomethylperfluorobiphenyl

HRID 1795310

Reaction equation

HRID 1795310 reaction equation
[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>>[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]

Participants

4

Reactant 3

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

Product 1

HCID 865911214-BromomethylperfluorobiphenylYield 60%

Procedure

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) andacarbon 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.

Workup

  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)

Sources & evidence

ORD record
ord-46bb7ecad4ac430ca08e02b95be2737b
Source dataset
uspto-grants-2006_04
Patent number
US07026409B2

Linked notes

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