1-Bromo-4-(prop-1-en-2-yl)benzene → 1-Bromo-4-isopropylbenzene

HRID 543871Notes

Reaction equation

HRID 543871 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([CH3:8])=[CH2:7])=[CH:4][CH:3]=1.[H][H]>[Pt]=O.C(O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]([CH3:8])[CH3:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 36144101-Bromo-4-(prop-1-en-2-yl)benzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 114621-Bromo-4-isopropylbenzeneYield 80.5%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A 23.2 g quantity of p-bromo-α-methylstyrene (118 mmole), approximately 100 mg platinum oxide, and 150 ml absolute ethanol were shaken on a Paar Hydrogenator for four hours, beginning with an initial hydrogen pressure of 50 psi. The material was then filtered through a celite plug and the solvent removed by distillation at atmospheric pressure. The residue resulting was distilled using a water aspirator vacuum to produce 18.9 g (80.4% yield) of p-bromocumene, bp 88°-92° C.

Workup

  1. filtrationThe material was then filtered through a celite plug
  2. customthe solvent removed by distillation at atmospheric pressure
  3. customThe residue resulting
  4. distillationwas distilled

Sources & evidence

ORD record
ord-ef8b82f307bf4b138860dfa34d9a2414
Source dataset
uspto-grants-1984_05
Patent number
US04447542

Reaction notes

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