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

HRID 512592Notes

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

Reactant 4

HCID 713Formamide

HCID 8857Ethyl Acetate

HCID 516892Sodium Bicarbonate

HCID 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

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

Sources & evidence

ORD record: ord-002b3e726f744cac9655081b525b41ef
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102643B2

Reaction notes

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