Water → 1-(2-Bromo-3,5,6-trimethylphenyl)ethanone

HRID 1985907Notes

Reaction equation

HRID 1985907 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[CH:4][C:3]=1[CH3:10].[C:11](Cl)(=[O:13])[CH3:12].[Cl-].[Al+3].[Cl-].[Cl-].O>ClCCl>[Br:1][C:2]1[C:3]([CH3:10])=[CH:4][C:5]([CH3:9])=[C:6]([CH3:8])[C:7]=1[C:11](=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 796101-Bromo-2,4,5-trimethylbenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 866136691-(2-Bromo-3,5,6-trimethylphenyl)ethanoneYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 1-bromo-2,4,5-trimethylbenzene (5.0 g, 25.0 mmol) and acetyl chloride (2.45 ml, 34.5 mmol) in dichloromethane (50 ml) was added aluminium chloride (4.42 g, 33.1 mmol) in dichloromethane (50 ml) and the reaction mixture was stirred at room temperature for 18 h. The mixture was poured into water and the two layers were separated. The organic phase was washed with saturated aqueous sodium hydrogen carbonate solution, dried (MgSO4) and filtered through silica. The filtrate was concentrated in vacuo to give the title compound (5.50 g).

Workup

  1. customthe two layers were separated
  2. washThe organic phase was washed with saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered through silica
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-df4779b1902f4751b652d7b877f1d292
Source dataset
uspto-grants-2009_06
Patent number
US07547718B2

Reaction notes

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