Allyl bromide → 1-Chloro-2-methyl-3-prop-2-enylbenzene

HRID 1656928Notes

Reaction equation

HRID 1656928 reaction equation
[CH3:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[Mg]Cl.[CH2:11](Br)[CH:12]=[CH2:13].C(=O)(O)[O-].[Na+]>ClCCl.C1COCC1.[Cl-].[Cl-].[Cl-].[V+3]>[Cl:8][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:13][CH:12]=[CH2:11])[C:2]=1[CH3:1]

Participants

7

Reactant 3

HCID 7841Allyl bromideHCID 516892Sodium BicarbonateHCID 178427904HCID 178427904, compound

Product 1

HCID 106786531-Chloro-2-methyl-3-prop-2-enylbenzeneYield 42.5%

Reagents, catalysts & solvents 3

HCID 178478626HCID 178478626, compoundCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

158 g of vanadium trichloride are dissolved in 800 ml of dichloromethane, and 500 ml of a solution of 1 mol of 2-methyl-3-chlorophenylmagnesium chloride in THF are added at 25° C. Stirring is carried out for 0.5 hour, after which 121 g of allyl bromide are added dropwise, stirring is effected for 10 hours at 25° C. and the mixture is then refluxed for 6 hours. The resulting reaction mixture is poured into 2 l of saturated, aqueous sodium bicarbonate solution and then extracted with methyl tertbutyl ether. 70.9 g of 1-chloro-2-methyl-3-prop-2-enylbenzene (bp. 78° C./1 mbar) are obtained by distillation.

Workup

  1. stirringstirring
  2. waitis effected for 10 hours at 25° C.
  3. temperaturethe mixture is then refluxed for 6 hours
  4. customThe resulting reaction mixture
  5. extractionextracted with methyl tertbutyl ether

Sources & evidence

ORD record
ord-1f3bd82c83b648a297ceef83099c35ef
Source dataset
uspto-grants-1993_10
Patent number
US05256666

Reaction notes

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