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

HRID 2359246Notes

Reaction equation

HRID 2359246 reaction equation
Br[CH:2]([CH3:16])[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:28]([NH2:30])=[O:29]>>[Br:13][C:8]1[C:9]([O:11][CH3:12])=[CH:10][C:5]([C:3]2[N:30]=[CH:28][O:29][C:2]=2[CH3:16])=[CH:6][C:7]=1[O:14][CH3:15]

Participants

5

Reactant 4

HCID 713FormamideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 584320252-Bromo-1-(4-bromo-3,5-dimethoxyphenyl)propan-1-one

Product 1

HCID 584319854-(4-Bromo-3,5-dimethoxyphenyl)-5-methyloxazoleYield 55%

Procedure

A solution of 2-bromo-1-(4-bromo-3,5-dimethoxyphenyl)propan-1-one (1.07 g, 3.04 mmol) in formamide (10 mL) in an oven-dried flask under argon was heated at 110° C. for 16 hrs. 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 (30% EtOAc-hexanes) gave 4-(4-bromo-3,5-dimethoxyphenyl)-5-methyloxazole as a yellow solid (0.496 g, 55% 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 (30% EtOAc-hexanes)

Sources & evidence

ORD record
ord-d034f457decc46109ed625390f4897af
Source dataset
uspto-grants-2014_04
Patent number
US08685975B2

Reaction notes

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