Carbon tetrabromide → HCID 178455712, compound

HRID 1034113Notes

Reaction equation

HRID 1034113 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@H:27]1[CH2:32][CH2:31][C@H:30]([C:33]2[CH:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][CH:34]=2)[CH2:29][CH2:28]1)[CH3:26]>ClCCl>[CH2:25]([C@H:27]1[CH2:28][CH2:29][C@H:30]([C:33]2[CH:34]=[CH:35][C:36]([CH:37]=[C:1]([Br:5])[Br:2])=[CH:39][CH:40]=2)[CH2:31][CH2:32]1)[CH3:26]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 178455716HCID 178455716, compound

Product 1

HCID 178455712HCID 178455712, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

148 g of carbon tetrabromide was dissolved in ml of dichloromethane, and 93 g of triphenylphospine was added at 0° C. or less. Next, 48.6 g of 4-(trans-4'-ethylcyclohexyl)benzaldehyde was dissolved in 225 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 of hexane was added to the residue. The resulting crystals were filtrated and further washed with hexane three times. The residue was subjected to recrystallization with hexane to obtain 52 g of 4-(trans-4'-ethylcyclohexyl)-β,β-dibromostyrene.

Workup

  1. additionwas added at 0° C. or less
  2. customAfter completion of the reaction
  3. distillationthe dichloromethane was distilled off
  4. addition500 ml of hexane was added to the residue
  5. filtrationThe resulting crystals were filtrated
  6. washfurther washed with hexane three times
  7. customThe residue was subjected to recrystallization with hexane

Sources & evidence

ORD record
ord-66e1eae8fcbd49a0a454f0a875f22706
Source dataset
uspto-grants-1994_05
Patent number
US05314640

Reaction notes

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