N-bromobutanimide → 4-Bromomethyl-3-fluorobiphenyl

HRID 1699638Notes

Reaction equation

HRID 1699638 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[Br:15]N1C(=O)CCC1=O>N(C(C)(C)C#N)=NC(C)(C)C#N.C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 161275023-Fluoro-4-methylbiphenyl

Product 1

HCID 186808134-Bromomethyl-3-fluorobiphenylYield 97.2%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-fluoro-4-methylbiphenyl (6.00 g), N-bromosuccinimide (5.73 g), 2,2′-azobisisobutyronitrile (0.075 g) and carbon tetrachloride (120 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, oily 4-bromomethyl-3-fluorobiphenyl (8.30 g) is obtained. 1H-NMR (CDCl3, δ): 4.57 (2H, s), 7.30 (1H, d, J=11.0 Hz), 7.34-7.40 (2H, m), 7.45 (3H, m), 7.56 (2H, d).

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-fb735d65984a4240b97cb732a7e41e4d
Source dataset
uspto-grants-2002_02
Patent number
US06348032B1

Reaction notes

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