Azobisisobutyronitrile → 4'-(Bromomethyl)-2-fluoro-1,1'-biphenyl

HRID 1699636Notes

Reaction equation

HRID 1699636 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1.[Br:15]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][C:11]([CH2:14][Br:15])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 114694992-Fluoro-4'-methyl-1,1'-biphenyl

Product 1

HCID 186809324'-(Bromomethyl)-2-fluoro-1,1'-biphenyl

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-fluoro-4′-methylbiphenyl (8.70 g), N-bromosuccinimide (8.32 g), 2,2′-azobisisobutyronitrile (0.10 g) and carbon tetrachloride (150 ml) is refluxed by heating for five hours. The reaction solution is washed with water. The residue, which is obtained by concentrating the organic layer, is purified using silica gel column chromatography (eluate: hexane/ethyl acetate=9/1) and thus, preliminarily purified 2-fluoro-4′-bromomethylbiphenyl is obtained. Furthermore, crystallization using hexane produced 2-fluoro-4′-bromomethylbiphenyl (4.93 g). 1H-NMR (CDCl3, δ): 4.55 (2H, s), 7.13-7.23 (2H, m), 7.33 (1H, m), 7.43 (1H, m), 7.47 (2H, d, J=8.1 Hz), 7.54 (2H, d, J=8.1 Hz).

Workup

  1. temperatureis refluxed
  2. temperatureby heating for five hours
  3. washThe reaction solution is washed with water
  4. customThe residue, which is obtained
  5. concentrationby concentrating the organic layer
  6. customis purified

Sources & evidence

ORD record
ord-3fd66f387260482dbc1d5e56dcc7742f
Source dataset
uspto-grants-2002_02
Patent number
US06348032B1

Reaction notes

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