1,1-Diphenylethylene → 2-Bromo-1,1-diphenylethylene

HRID 1282461Notes

Reaction equation

HRID 1282461 reaction equation
[C:1]1([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:15]Br>C(Cl)(Cl)(Cl)Cl>[Br:15][CH:8]=[C:7]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 107401,1-DiphenylethyleneHCID 24408Bromine

Product 1

HCID 2629142-Bromo-1,1-diphenylethyleneYield 81%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

Into a reactor were introduced 110 g (0.60 mol) of the 1,1-diphenylethylene and 1,098 g of carbon tetrachloride under a nitrogen atmosphere. A solution prepared by mixing 95.9 g (0.60 mol) of bromine with 288 g of carbon tetrachloride was added dropwise thereto over 1 hour with cooling with ice. After completion of the addition, the reaction mixture was stirred at that temperature for 7 hours and then concentrated. To the residue were added 119 g of pyridine and 500 mL of toluene. This mixture was refluxed for 3 hours. After being cooled, the reaction mixture was washed with 5% hydrochloric acid and water, subsequently dried with anhydrous sodium sulfate, and then concentrated under reduced pressure. The resultant concentrate was distilled and then recrystallized from methanol to obtain 126 g (81%) of the target compound as white crystals.

Workup

  1. customA solution prepared
  2. additionwas added dropwise
  3. temperatureover 1 hour with cooling with ice
  4. additionAfter completion of the addition
  5. concentrationconcentrated
  6. additionTo the residue were added 119 g of pyridine and 500 mL of toluene
  7. temperatureThis mixture was refluxed for 3 hours
  8. temperatureAfter being cooled
  9. washthe reaction mixture was washed with 5% hydrochloric acid and water
  10. dry with materialsubsequently dried with anhydrous sodium sulfate
  11. concentrationconcentrated under reduced pressure
  12. concentrationThe resultant concentrate
  13. distillationwas distilled
  14. customrecrystallized from methanol

Sources & evidence

ORD record
ord-0a9b09ff78fb41cdb06e05ac98eadb52
Source dataset
uspto-grants-2002_09
Patent number
US06455720B1

Reaction notes

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