Allyl bromide → HCID 20082700, compound

HRID 467057Notes

Reaction equation

HRID 467057 reaction equation
[Mg].[Cl:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8]Br)=[CH:5][CH:4]=1.[CH2:12](Br)[CH:13]=[CH2:14]>CCOCC>[Cl:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8][CH2:14][CH:13]=[CH2:12])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 230291-(2-Bromoethyl)-4-chlorobenzeneHCID 5462224Magnesium

Product 1

HCID 20082700HCID 20082700, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a flame-dried flask containing 7.75 g of magnesium turnings under ether was added 4-chlorophenethyl bromide (70 g) in anhydrous ether (250 mL) at such a rate as to maintain a gentle reflux. When the addition was complete, the mixture was heated under reflux for an additional hour and then treated dropwise over one hour with allyl bromide (27.6 mL, 38.6 g) in ether (75 mL) maintaining a gentle reflux. The resulting mixture was stirred overnight at room temperature and then poured onto 600 mL of ice-cold dilute sulfuric acid. The product was extracted with ethyl acetate and the combined extracts were washed with dilute aqueous potassium carbonate, dried (MgSO4) and evaporated. The resulting brown oil was distilled under reduced pressure to give 43 g of 5-(4-chlorophenyl)pent-1-ene, b.p. 74°-80° (2 mmHg) as a colorless liquid.

Workup

  1. temperatureto maintain a gentle reflux
  2. additionWhen the addition
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for an additional hour
  5. temperaturemaintaining a gentle reflux
  6. extractionThe product was extracted with ethyl acetate
  7. washthe combined extracts were washed with dilute aqueous potassium carbonate
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. distillationThe resulting brown oil was distilled under reduced pressure

Sources & evidence

ORD record
ord-53c25b08e4374d8bb8095ade29bb032a
Source dataset
uspto-grants-1992_10
Patent number
US05158949

Reaction notes

Loading…