3-Methylacetophenone → 1-(3-(Bromomethyl)phenyl)ethan-1-one

HRID 1356777

Reaction equation

HRID 1356777 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[Br:11]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 114553-MethylacetophenoneHCID 67184N-bromobutanimide

Product 1

HCID 154798071-(3-(Bromomethyl)phenyl)ethan-1-oneYield 38.8%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

3′-Methylacetophenone (5.00 g; 37.3 mmol), N-bromosuccinimide (6.63 g; 37.3 mmol), and benzoyl peroxide (100 mg) were added to carbon tetrachloride (70 ml), and the mixture was refluxed for 1 hour. The mixture was left to cool to room temperature, and crystals that precipitated were removed by filtration. The filtrate was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1), to thereby yield 3.08 g of the target compound (yield: 38.8%).

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. waitThe mixture was left
  3. customcrystals that precipitated
  4. customwere removed by filtration
  5. customThe filtrate was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-fabc5a7317ba403681b8e1ab8e4315af
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Linked notes

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