Bromide ion → 4,4'-Dichlorobiphenyl

HRID 329313Notes

Reaction equation

HRID 329313 reaction equation
[Br-].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([Mg]Br)=[CH:5][CH:4]=1>C1C=CC=CC=1.O1CCCC1>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:6]2[CH:7]=[CH:8][C:3]([Cl:2])=[CH:4][CH:5]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 259Bromide ionHCID 178478191HCID 178478191, compound

Product 1

HCID 163084,4'-Dichlorobiphenyl

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Thallous bromide (22.46 gm, 0.079 mole) is added to a solution of p-chlorophenyl magnesium bromide (0.0395 mole) in a mixture of benzene (25 ml.) and tetrahydrofuran (25 ml.) and the mixture stirred and refluxed under nitrogen for 7 hours. The reaction mixture is cooled, poured into 150 ml. of dilute hydrochloric acid, and the 4,4'-dichlorobiphenyl extracted with ether (2 × 30 ml.). The combined extracts are dried over anhydrous sodium sulfate, and the solvent removed to leave 2.9 gm. of crude white product. This is filtered through a short column of alumina using chloroform as eluent, to give, after removal of the solvent, 2.70 gm. (61%) of pure 4,4'-dichlorobiphenyl, m.p. 148°.

Workup

  1. temperaturerefluxed under nitrogen for 7 hours
  2. temperatureThe reaction mixture is cooled
  3. additionpoured into 150 ml
  4. extractionof dilute hydrochloric acid, and the 4,4'-dichlorobiphenyl extracted with ether (2 × 30 ml.)
  5. dry with materialThe combined extracts are dried over anhydrous sodium sulfate
  6. customthe solvent removed
  7. customto leave 2.9 gm
  8. filtrationThis is filtered through a short column of alumina
  9. customto give
  10. customafter removal of the solvent, 2.70 gm

Sources & evidence

ORD record
ord-311ba20ae15748cab694e6f7d6740053
Source dataset
uspto-grants-1977_04
Patent number
US04020073

Reaction notes

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