Bromobenzene → 3-Ethenyl-1,1'-biphenyl

HRID 1653827Notes

Reaction equation

HRID 1653827 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=[CH2:13]>C(OCC)C>[C:2]1([C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH:12]=[CH2:13])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7961BromobenzeneHCID 748703-Bromostyrene

Product 1

HCID 207231583-Ethenyl-1,1'-biphenylYield 81.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The liquid temperature was increased until refluxing took place and then a solution of 7.37 g (0.07 mole) of bromobenzene in diethyl ether (70 ml) was gradually added dropwise taking 30 minutes. After completion of the dropwise addition, it was kept as such for 1 hour under reflux. The reaction solution was cooled to room temperature and it was added at room temperture to a solution of 6.51 ml (0.05 mole) of m-bromostyrene and 0.32 g (0.6 m mole) of a nickel chloride-(1,3-diphenyl phosphino propane) complex in diethyl ether (100 ml). After completion of the dropwise addition, refluxing was continued for 4 hours. The reaction solution was poured into 500 ml of ice water and the pH was adjusted to be weakly acidic. Extraction with hexane was undertaken and, through washing, drying, removal of the solvent by distillation and purification by the silica gel column chromatography, 7.32 g of m-phenyl styrene (yield 80%) were obtained.

Workup

  1. temperatureThe liquid temperature was increased
  2. temperatureuntil refluxing
  3. additionAfter completion of the dropwise addition, it
  4. customsuch for 1 hour
  5. temperatureunder reflux
  6. additionAfter completion of the dropwise addition
  7. temperaturerefluxing
  8. waitwas continued for 4 hours
  9. extractionExtraction with hexane
  10. washthrough washing
  11. customdrying
  12. customremoval of the solvent
  13. distillationby distillation and purification by the silica gel column chromatography

Sources & evidence

ORD record
ord-53c7a6f7d7f94ca5ab7348994ab6cbc2
Source dataset
uspto-grants-1995_04
Patent number
US05403908

Reaction notes

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