Carbon tetrabromide → HCID 19023069, compound

HRID 1034110Notes

Reaction equation

HRID 1034110 reaction equation
[C:1]([Br:5])(Br)(Br)[Br:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:25]([C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][C:38]([CH:41]=O)=[CH:37][CH:36]=2)=[CH:31][CH:30]=1)[CH2:26][CH2:27][CH3:28]>ClCCl>[CH2:25]([C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:36]=[CH:37][C:38]([CH:41]=[C:1]([Br:5])[Br:2])=[CH:39][CH:40]=2)=[CH:31][CH:30]=1)[CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 1782563HCID 1782563, compound

Product 1

HCID 19023069HCID 19023069, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

60 g of carbon tetrabromide was dissolved in 185 ml of dichloromethane, and 100 g of triphenylphosphine was added at 0° C. or less. Next, 22 g of 4'-butyl-4-biphenylaldehyde was dissolved in 93 ml of dichloromethane, which then was added dropwise to the first dichloromethane solution over a period of one hour. The combined solutions were then agitated at room temperature for one hour. After completion of the reaction, the dichloromethane was distilled off, and 500 ml hexane was added to the residue. The resulting crystals were filtrated and further washed with hexane three times. The residue was recrystallized with hexane to obtain 9.6 g of 4-(4'-butylphenyl)-β,β-dibromostyrene.

Workup

  1. customAfter completion of the reaction
  2. distillationthe dichloromethane was distilled off
  3. addition500 ml hexane was added to the residue
  4. filtrationThe resulting crystals were filtrated
  5. washfurther washed with hexane three times
  6. customThe residue was recrystallized with hexane

Sources & evidence

ORD record
ord-ec7646acc134490aaf7403592d6bd62c
Source dataset
uspto-grants-1994_05
Patent number
US05314640

Reaction notes

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