p-Bromochlorobenzene → 1-Allyl-4-chlorobenzene

HRID 2107063Notes

Reaction equation

HRID 2107063 reaction equation
[Mg].[Cl:2][C:3]1[CH:8]=[CH:7][C:6](Br)=[CH:5][CH:4]=1.[CH2:10](Br)[CH:11]=[CH2:12].[Cl-].[NH4+]>CCOCC>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:12][CH:11]=[CH2:10])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 7806p-BromochlorobenzeneHCID 7841Allyl bromideHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 110190641-Allyl-4-chlorobenzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a suspension of magnesium turnings (9.6 g) in anhydrous ether (50 ml) was added dropwise to a solution of p-chlorobromobenzene (76.6 g) in anhydrous ether (500 ml) at such a rate as to maintain reflux. After refluxing for a further 20 minutes, the solution was cooled to 5o and a solution of allyl bromide (48.4 g) in anhydrous ether (100 ml) was added over 15 minutes. After 30 minutes the solution was allowed to warm to room temperature, and then saturated ammonium chloride was added dropwise, cautiously to avoid excessive frothing. The organic layer was separated and the aqueous phase was extracted with ether. After washing the ether extracts with water and drying, evaporation of the solvent gave a pale yellow oil which was purified by fractional distillation to give 3-(4-chlorophenyl)prop-1-ene as a colourless oil, b.p. 72°-74°/4 mm Hg. (532 Pa).

Workup

  1. temperatureto maintain
  2. temperaturereflux
  3. temperatureAfter refluxing for a further 20 minutes
  4. customThe organic layer was separated
  5. extractionthe aqueous phase was extracted with ether
  6. washAfter washing the ether
  7. customdrying
  8. customevaporation of the solvent
  9. customgave a pale yellow oil which
  10. distillationwas purified by fractional distillation

Sources & evidence

ORD record
ord-8f051d5146a3433f82cc5b85d57b93ba
Source dataset
uspto-grants-1990_06
Patent number
US04933357

Reaction notes

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