4-Bromophenacyl bromide → 4-(4-Bromophenyl)-1,3-oxazole

HRID 2086665Notes

Reaction equation

HRID 2086665 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=O.[CH:12]([O-:14])=O.[NH4+:15].[OH-].[Na+]>C(O)=O>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:15]=[CH:12][O:14][CH:2]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 74544-Bromophenacyl bromideHCID 14798Sodium HydroxideHCID 2723923Ammonium formate

Product 1

HCID 223165954-(4-Bromophenyl)-1,3-oxazoleYield 26%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a stirred solution of 2,4′-dibromoacetophenone (9.66 g, 34.8 mmol) in formic acid (42 ml) was added ammonium formate (7.58 g, 120.6 mmol), and the mixture was heated at reflux temperature for 3 hours. The reaction mixture was cooled down to room temperature, and made basic by addition of 50% NaOH aqueous solution. The whole was extracted with CH2H2. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate-hexane (1:5) to give title compound (2.0 g, 26% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 3 hours
  3. extractionThe whole was extracted with CH2H2
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography
  8. washeluting with ethyl acetate-hexane (1:5)

Sources & evidence

ORD record
ord-dec27687a2ca45bdbe8cddbed35967d6
Source dataset
uspto-grants-2004_04
Patent number
US06727238B2

Reaction notes

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