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

HRID 2041566Notes

Reaction equation

HRID 2041566 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C1C(=O)N([Br:18])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([CH2:1][Br:18])=[CH:3][CH:4]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 2

HCID 8500p-METHYLACETOPHENONEHCID 67184N-bromobutanimide

Product 1

HCID 5837851-[4-(Bromomethyl)phenyl]ethan-1-oneYield 65.4%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Heat a mixture of 4′-methylacetophenone (5 g, 37.26 mmol), NBS (6.964 g, 39.12 mmol), and AIBN (153 mg, 0.93 mmol) in carbon tetrachloride (120.mL) for 14 h at reflux. Cool to ambient temperature and wash sequentially with water (100 mL), 1M aqueous HCl (100 mL), 5% aqueous NaHCO3 (100 mL) and brine (100 mL). Dry the organic phase over Na2SO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting sequentially with hexane and hexane/EtOAc (19:1, 9:1) to provide the title compound as oil (5.191 g, 65%). GC-MS m/z: 213 (M+).

Workup

  1. temperatureHeat
  2. temperatureat reflux
  3. washwash sequentially with water (100 mL), 1M aqueous HCl (100 mL), 5% aqueous NaHCO3 (100 mL) and brine (100 mL)
  4. dry with materialDry the organic phase over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify the crude mixture by chromatography on silica gel eluting sequentially with hexane and hexane/EtOAc (19:1, 9:1)

Sources & evidence

ORD record
ord-bf6e6aebb7014c29907e7eeac64bfda3
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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