4-Bromotoluene → HCID 19604611, compound

HRID 1653828Notes

Reaction equation

HRID 1653828 reaction equation
Br[CH2:2][CH2:3]Br.[Mg].Br[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1.BrC1C=[CH:21][C:18]([CH:19]=[CH2:20])=[CH:17][CH:16]=1>C(OCC)C>[CH:2]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)=[CH2:3]

Participants

6

Reactant 4

HCID 78054-BromotolueneHCID 78391,2-DibromoethaneHCID 162634-BromostyreneHCID 5462224Magnesium

Product 1

HCID 19604611HCID 19604611, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

Under a stream of an inert gas with agitation, a drop of 1,2-dibromoethane was added to a diethyl ether (100 ml) solution of 1.70 g (0.07 mole) of granular metallic magnesium and the Grignard reagent reaction was started by heating. The liquid temperature was increased up to refluxing and then a diethyl ether (70 ml) solution of 8.61 ml (0.07 mole) of p-bromotoluene was gradually added dropwise taking 30 minutes. After completion of the dropwise addition, it was kept standing under reflux for 1 hour. The reaction solution was cooled to room temperature and it was added dropwise, at room temperature, to a diethyl ether (100 ml) solution of 6.54 ml (0.05 mole) of p-bromo-styrene and 0.32 g (0.6 mmole) of a nickel chloride-(1,3-diphenyl phosphino propane) complex. 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 was made with hexane and, through purification by washing, drying, removal of the solvent by distillation and silica gel column chromatography, 7.28 g (yield 75%) of 4-vinyl-4'-methyl biphenyl were obtained.

Workup

  1. temperatureby heating
  2. temperatureThe liquid temperature was increased up
  3. temperatureto refluxing
  4. additionAfter completion of the dropwise addition, it
  5. temperatureunder reflux for 1 hour
  6. additionAfter completion of the dropwise addition
  7. temperaturerefluxing
  8. waitwas continued for 4 hours
  9. extractionExtraction
  10. customwas made with hexane and, through purification
  11. washby washing
  12. customdrying
  13. customremoval of the solvent
  14. distillationby distillation and silica gel column chromatography

Sources & evidence

ORD record
ord-2c3cee06b82846b3bd013d183486930e
Source dataset
uspto-grants-1995_04
Patent number
US05403908

Reaction notes

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