p-Methylpropiophenone → 2-Bromo-1-(4-methylphenyl)propan-1-one

HRID 2308745Notes

Reaction equation

HRID 2308745 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[Br:16]Br>C(Cl)(Cl)Cl>[Br:16][CH:9]([CH3:10])[C:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:11]

Participants

5

Reactant 3

HCID 21429p-MethylpropiophenoneHCID 24408BromineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27340632-Bromo-1-(4-methylphenyl)propan-1-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

14.8 g (0.1 mol) of 4'-methylpropiophenone are introduced into 100 ml of chloroform, in the presence of a small amount of finely ground aluminium chloride, and a solution of 15.9 g (0.1 mol; 5 ml) of bromine, in 20 ml of chloroform is added dropwise whilst cooling with an ice bath. The mixture is left to react overnight at ambient temperature. It is then filtered, the solvent is evaporated off from the filtrate and the crystalline residue is washed with diethyl ether. 21.5 g of crystals are collected.

Workup

  1. temperaturewhilst cooling with an ice bath
  2. waitThe mixture is left
  3. customto react overnight at ambient temperature
  4. filtrationIt is then filtered
  5. customthe solvent is evaporated off from the filtrate
  6. washthe crystalline residue is washed with diethyl ether
  7. custom21.5 g of crystals are collected

Sources & evidence

ORD record
ord-df5e92b00215465884ea7028ed5799ef
Source dataset
uspto-grants-1987_09
Patent number
US04690931

Reaction notes

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