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

HRID 1276931Notes

Reaction equation

HRID 1276931 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>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

4

Reactant 2

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

Product 1

HCID 186809324'-(Bromomethyl)-2-fluoro-1,1'-biphenylYield 39.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 8.70 g of 2-fluoro-4'-methylbiphenyl, 8.32 g of N-bromosuccinimide, 0.10 g of 2,2'-azobisisobutylonitrile and 150 ml of carbon tetrachloride was heat-refluxed for 5 hours. The reaction solution was washed with water, and the organic layer was concentrated. The resulting residue was purified through silica-gel column chromatography (eluent: a mixture of hexane and ethyl acetate at a ratio of 9:1) to obtain crude 2-fluoro-4'-bromomethylbiphenyl. Further, this compound was crystallized from hexane to give 4.93 g of 2-fluoro-4'-bromomethylbiphenyl.

Workup

  1. temperaturewas heat-refluxed for 5 hours
  2. washThe reaction solution was washed with water
  3. concentrationthe organic layer was concentrated
  4. customThe resulting residue was purified through silica-gel column chromatography (eluent
  5. additiona mixture of hexane and ethyl acetate at a ratio of 9:1)
  6. customto obtain crude 2-fluoro-4'-bromomethylbiphenyl
  7. customFurther, this compound was crystallized from hexane

Sources & evidence

ORD record
ord-b3776a8dc11f4738ba4b3e850ae13eea
Source dataset
uspto-grants-2000_12
Patent number
US06166219

Reaction notes

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