1-(3-Bromo-5-nitrophenyl)ethanol → Ethanone, 1-(3-bromo-5-nitrophenyl)-

HRID 221708Notes

Reaction equation

HRID 221708 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:11]([OH:13])[CH3:12])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:11](=[O:13])[CH3:12])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

3

Reactant 1

HCID 666658361-(3-Bromo-5-nitrophenyl)ethanol

Product 1

HCID 182852Ethanone, 1-(3-bromo-5-nitrophenyl)-

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-(3-Bromo-5-nitro-phenyl)-ethanol (12.84 g, 52.2 mmol) was dissolved in dioxane (245 ml) and manganedioxide (31.8 g, 365 mmol) was added. The reaction was refluxed for 17 hrs. The reaction was filtered and solvent was removed under reduced pressure yielding the title compound as yellow solid. 1H-NMR (500 MHz, DMSO-d6): 8.64 (s, 1H), 8.58 (s, 1H), 8.53 (s, 1H), 2.70 (s, 3H); GC/MS: 243 [(M)+].

Workup

  1. additionmanganedioxide (31.8 g, 365 mmol) was added
  2. temperatureThe reaction was refluxed for 17 hrs
  3. filtrationThe reaction was filtered
  4. customsolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9a56ee13bb6c4ed79fec184a713f12dc
Source dataset
uspto-grants-2012_06
Patent number
US08207164B2

Reaction notes

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