Carbon tetrabromide → HCID 178447860, compound

HRID 1034115Notes

Reaction equation

HRID 1034115 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:28]1[CH2:33][CH2:32][C@H:31]([C:34]2[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=2)[CH2:30][CH2:29]1)[CH2:26][CH3:27]>ClCCl>[CH2:25]([C@H:28]1[CH2:33][CH2:32][C@H:31]([C:34]2[CH:35]=[CH:36][C:37]([CH:38]=[C:1]([Br:5])[Br:2])=[CH:40][CH:41]=2)[CH2:30][CH2:29]1)[CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 178447881HCID 178447881, compound

Product 1

HCID 178447860HCID 178447860, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

26.9 g of carbon tetrabromide was dissolved in 82 ml of dichloromethane, and 42.6 g of triphenylphosphine was added at 0° C. or less. Next, 10 g of 4-(trans-4'-propylcyclohexyl)benzaldehyde was dissolved in 41 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 washed with hexane three times. The residue was subjected to recrystallization with hexane to obtain 16 g of 4-(trans-4'-propylcyclohexyl)-β,β-dibromostyrene.

Workup

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

Sources & evidence

ORD record
ord-a89b3213b3bd43d2ba6a9f286c49990a
Source dataset
uspto-grants-1994_05
Patent number
US05314640

Reaction notes

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