p-METHYLACETOPHENONE → 1-[4-(Bromomethyl)phenyl]ethan-1-one

HRID 2200557Notes

Reaction equation

HRID 2200557 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:10])=[O:9])=[CH:6][CH:7]=1.[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:9])[CH3:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8500p-METHYLACETOPHENONEHCID 67184N-bromobutanimide

Product 1

HCID 5837851-[4-(Bromomethyl)phenyl]ethan-1-oneYield 71.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 1-p-tolylethanone (600 mg, 4.47 mmol) in carbon tetrachloride (15 mL) was added N-bromosuccinimide (955 mg, 5.37 mmol) and BPO (31 mg, 0.13 mmol). The mixture was refluxed for 3 h; then it was cooled, and filtered. The filtrate was concentrated to give 1-(4-(bromomethyl)phenyl)ethanone (683 mg, 71%) as a brown oil. LCMS MH+ 213.

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. temperaturethen it was cooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f7e05d3384964ecda9f2682b8cc6c3cd
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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