Azobisisobutyronitrile → 2-(3-Bromomethyl-indazol-1-yl)-benzonitrile

HRID 1481889Notes

Reaction equation

HRID 1481889 reaction equation
CC(N=NC(C#N)(C)C)(C#N)C.C1C(=O)N([Br:20])C(=O)C1.[CH3:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]([C:31]2[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=2[C:33]#[N:34])[N:23]=1>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]([C:31]2[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=2[C:33]#[N:34])[N:23]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 900375452-(3-methyl-1H-indazol-1-yl)benzonitrile

Product 1

HCID 900376452-(3-Bromomethyl-indazol-1-yl)-benzonitrileYield 93.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

AIBN (141 mg, 0.857 mmol) and NBS (839 mg, 4.72 mmol) were added to a suspension of 2-(3-methyl-1H-indazol-1-yl)benzonitrile (1 g, 4.29 mmol) in CCl4 (20 mL) and the mixture heated to reflux for 2 h. The mixture was concentrated and the residue purified by silica gel chromatography to give the title compound (1.25 g, 93%) as an off white solid.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 2 h
  3. concentrationThe mixture was concentrated
  4. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-66c9f74b616f4df1b0ab749f18d91284
Source dataset
uspto-grants-2016_08
Patent number
US09409888B2

Reaction notes

Loading…