Hydrochloric Acid → 1-(2-Bromoprop-2-en-1-yl)-4-chlorobenzene

HRID 1265970Notes

Reaction equation

HRID 1265970 reaction equation
[Br:1][C:2]([CH2:4]Br)=[CH2:3].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([Mg]Br)=[CH:9][CH:8]=1.Cl>C(OCC)C>[Br:1][C:2](=[CH2:3])[CH2:4][C:10]1[CH:11]=[CH:12][C:7]([Cl:6])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 105522,3-DibromopropeneHCID 178478191HCID 178478191, compound

Product 1

HCID 100368921-(2-Bromoprop-2-en-1-yl)-4-chlorobenzeneYield 83.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 8 ml (0.0622 mol) of 2,3-dibromopropene in 50 ml diethyl ether was placed under a nitrogen atmosphere by use of a Firestone valve. While cooling in an ice water bath, a solution of 62 ml (0.062 mol) of 1M 4-chlorophenylmagnesium bromide in diethyl ether was added slowly via addition funnel. After stirring for 2 hours while warming to room temperature, the reaction was recooled in an ice bath and 50 ml of 1 N hydrochloric acid was then added via syringe. The resulting mixture was transferred to a separatory funnel and the phases were separated. The organic layer was dried over MgSO4 and filtered. The solvent was removed from the filtrate in vacuo. The residue was triturated with cold pentanes to yield 12.0 g of 1-(2-bromo-allyl)-4-chloro-benzene as an oil which was used in without further purification.

Workup

  1. temperatureWhile cooling in an ice water bath
  2. customthe reaction was recooled in an ice bath
  3. customThe resulting mixture was transferred to a separatory funnel
  4. customthe phases were separated
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed from the filtrate in vacuo
  8. customThe residue was triturated with cold pentanes

Sources & evidence

ORD record
ord-879948f9dd66455ca47f51561b47d8bf
Source dataset
uspto-grants-2003_04
Patent number
US06548448B2

Reaction notes

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