Formamide → 4-(4-Bromo-3,5-dimethoxyphenyl)oxazole

HRID 2359152Notes

Reaction equation

HRID 2359152 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([Br:13])=[C:7]([O:14][CH3:15])[CH:6]=1)=O.CCOC(C)=O.C([O-])(O)=O.[Na+].[CH:27]([NH2:29])=[O:28]>>[Br:13][C:8]1[C:9]([O:11][CH3:12])=[CH:10][C:5]([C:3]2[N:29]=[CH:27][O:28][CH:2]=2)=[CH:6][C:7]=1[O:14][CH3:15]

Participants

5

Reactant 4

HCID 713FormamideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 584320022-Bromo-1-(4-bromo-3,5-dimethoxyphenyl)ethanone

Product 1

HCID 584321254-(4-Bromo-3,5-dimethoxyphenyl)oxazoleYield 58%

Procedure

A solution of 2-bromo-1-(4-bromo-3,5-dimethoxyphenyl)ethanone (0.8 g, 0.96 mmol) in formamide (7 mL) in an oven-dried flask under argon was heated at 100° C. for 10 hours then 110° C. for 5 hours. After cooling to room temp, EtOAc and saturated aqueous NaHCO3 were carefully added and the mixture was stirred for 15 minutes. It was then extracted with EtOAc twice and the combined organics were washed with H2O and brine, dried over Na2SO4 and concentrated. Purification by chromatography (20-40% EtOAc-hexanes) provided 4-(4-bromo-3,5-dimethoxyphenyl)oxazole as a yellow solid (0.387 g, 58% yield).

Workup

  1. extractionIt was then extracted with EtOAc twice
  2. washthe combined organics were washed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by chromatography (20-40% EtOAc-hexanes)

Sources & evidence

ORD record
ord-22b1211f86ea408186280db63b242566
Source dataset
uspto-grants-2014_04
Patent number
US08685975B2

Reaction notes

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