1,4-Diacetylbenzene → 1-(4-Acetylphenyl)-2-bromo-1-ethanone

HRID 497213Notes

Reaction equation

HRID 497213 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Br:13]Br>C(OCC)C.O.[Cl-].[Al+3].[Cl-].[Cl-]>[C:10]([C:7]1[CH:8]=[CH:9][C:4]([C:1](=[O:3])[CH2:2][Br:13])=[CH:5][CH:6]=1)(=[O:12])[CH3:11]

Participants

6

Reactant 2

HCID 138881,4-DiacetylbenzeneHCID 24408Bromine

Product 1

HCID 149132991-(4-Acetylphenyl)-2-bromo-1-ethanoneYield 88.8%

Reagents, catalysts & solvents 3

HCID 6451240Aluminum(III) ChlorideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 1,4-diacetylbenzene (5.3 g, 32.7 mmol), aluminum chloride (0.05 g, 0.38 mmol) in diethylether (50 ml) was added bromine (5.3 g, 32.7 mmol) dropwise over 20 minutes. The mixture was stirred for 30 minutes, and diluted with water. The whole was concentrated to remove diethylether, and the aqueous suspension was filtered to give 7.0 g of white solid. The compound was used for next reaction without purification.

Workup

  1. concentrationThe whole was concentrated
  2. customto remove diethylether
  3. filtrationthe aqueous suspension was filtered

Sources & evidence

ORD record
ord-51c10d8c02a449f0b3274ef84328c10f
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

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