P-Xylene → 2-Bromo-1-(2,5-dimethylphenyl)ethan-1-one

HRID 1871608Notes

Reaction equation

HRID 1871608 reaction equation
[C:1]1([CH3:8])[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1.[Br:9][CH2:10][C:11](Cl)=[O:12].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[Br:9][CH2:10][C:11]([C:2]1[CH:3]=[C:4]([CH3:7])[CH:5]=[CH:6][C:1]=1[CH3:8])=[O:12]

Participants

5

Reactant 3

HCID 7809P-XyleneHCID 89602Bromoacetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 126100412-Bromo-1-(2,5-dimethylphenyl)ethan-1-oneYield 105.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

A mixture of 10.60 g (0.10 mol) of para-xylene and 16.53 g (0.105 mol) of α-bromoacetyl chloride in 300 mL of 1,2dichloroethane was cooled in an ice bath under an atmosphere of dry N2 and treated portionwise with 14.15 g (0.106 mol) of aluminum chloride. The reaction mixture was stirred for 30 minutes at 0-5° C. and then for 2.5 hours at room temperature. The mixture was then poured onto ice and the aqueous layer was acidified with concentrated HCL. The organic layer was separated and the aqueous layer was extracted twice with methylene dichloride. The combined organic extracts were dried with brine solution and with magnesium sulfate. The solvent was evaporated to give 23.87 g of an amber oil which was for use in the next reaction without further purification.

Workup

  1. temperaturewas cooled in an ice bath under an atmosphere of dry N2
  2. waitfor 2.5 hours at room temperature
  3. additionThe mixture was then poured onto ice
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted twice with methylene dichloride
  6. dry with materialThe combined organic extracts were dried with brine solution and with magnesium sulfate
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-361e978ff43145b79f3d6969224abc1c
Source dataset
uspto-grants-2000_08
Patent number
US06103900

Reaction notes

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