1-Bromo-4-iodobenzene → Benzene, 1-bromo-4-(2-propenyl)-

HRID 1417869Notes

Reaction equation

HRID 1417869 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[CH2:9]([Mg]Br)[CH:10]=[CH2:11]>C(OCC)C.[Cu](Cl)(Cl)(Cl)Cl.[Li].[Li]>[CH2:11]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[CH:10]=[CH2:9]

Participants

5

Reactant 2

HCID 115221-Bromo-4-iodobenzeneHCID 178455850HCID 178455850, compound

Product 1

HCID 137529Benzene, 1-bromo-4-(2-propenyl)-

Reagents, catalysts & solvents 2

HCID 178478940HCID 178478940, compoundCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture comprising 4-bromo-iodobenzene (350 mmol), dilithium copper tetrachloride (15 mmol), and 500 ml of diethyl ether, was added dropwise 1M solution of allyl magnesium bromide on the market (corresponding to 300 mmol) in diethyl ether at a temperature lower than 10° C. in 2 hours. The solvent was removed under a reduced pressure and the residue was distilled under a reduced pressure to obtain a crude oily 4-allyl-bromobenzene. This product was rectified with an Oldershow column (number of theoretical plates is 10) to obtain 4-allyl-bromobenzene (127 mmol) as the distillate at 130°-134° C./9 mmHg.

Workup

  1. customThe solvent was removed under a reduced pressure
  2. distillationthe residue was distilled under a reduced pressure
  3. customto obtain a crude oily 4-allyl-bromobenzene

Sources & evidence

ORD record
ord-5a8b4cd4cdb04c81b820a5789be3fe05
Source dataset
uspto-grants-1999_03
Patent number
US05879585

Reaction notes

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