Hydrochloric Acid → 1-(3-Bromo-1,2-oxazol-5-yl)ethan-1-one

HRID 1061269Notes

Reaction equation

HRID 1061269 reaction equation
[Br:1][C:2](Br)=[N:3][OH:4].[CH3:6][C:7](=[O:10])[C:8]#[CH:9].C(=O)([O-])[O-].[K+].[K+].Cl>C(Cl)Cl>[Br:1][C:2]1[CH:9]=[C:8]([C:7](=[O:10])[CH3:6])[O:4][N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 15018Butyn-2-oneHCID 27632191-bromo-N-hydroxymethanecarbonimidoyl bromide

Product 1

HCID 136269711-(3-Bromo-1,2-oxazol-5-yl)ethan-1-oneYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of dibromoformaldoxime(which was obtained in Example 116) (32.5 g, 160.2 mmol), 3-butyn-one (13.41 g, 197 mmol), potassium carbonate (11 g, 80.1 mmol), and methylene chloride (300 mL) was stirred at ambient temperature for 20 hours. The slurry was then treated with aqueous hydrochloric acid (2N, 200 mL) and extracted with methylene chloride. The combined organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (ethyl acetate/hexanes 5/95) gave a white solid (16.76 g, 56% yield); 1H NMR (300 MHz, CDCl3) δ 2.62 (s, 3H), 6.97 (s, 1H).

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. customEvaporation and purification by flash chromatography (ethyl acetate/hexanes 5/95)

Sources & evidence

ORD record
ord-6e34349ad4eb47988318211609f94385
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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