Hydrochloric Acid → 1-[3-(4-Bromophenyl)-5-methyl-4-isoxazolyl]ethanone

HRID 132602Notes

Reaction equation

HRID 132602 reaction equation
[C:1]([CH2:4][C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].[O-]CC.[Na+].[Br:12][C:13]1[CH:18]=[CH:17][C:16](/[C:19](/Cl)=[N:20]/O)=[CH:15][CH:14]=1.Cl>CCO>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:4]([C:5](=[O:7])[CH3:6])=[C:1]([CH3:2])[O:3][N:20]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31261AcetylacetoneHCID 2723922Sodium ethoxideHCID 124408854-Bromo-N-hydroxybenzene-1-carboximidoyl chloride2×

Product 1

HCID 212961521-[3-(4-Bromophenyl)-5-methyl-4-isoxazolyl]ethanoneYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Acetylacetone (1.25 mL, 12 mmol) was added to a sodium ethoxide solution 3.09 N (3.95 mL, 12 mmol) in EtOH (22 mL) at room temperature. The resulting yellow solution was cooled with a ice-bath and a cloudy solution of (E)- and/or (Z)-4-bromo-N-hydroxy-benzenecarboximidoyl chloride (2.35 g, 10 mmol) in EtOH (8 mL) was added dropwise within 10 min keeping the temperature below 5° C. The light yellow suspension was stirred at room temperature for 3 h and then acidified with 6 N HCl and then evaporated. The resulting mixture was extracted with ethyl acetate and the combined organic layers were then washed with water and brine, dried over Na2SO4 and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate:=100:0 to 7:3) afforded the title compound (2.35 g, 84%) as a light yellow oil. MS m/e: 280.1/282.1 [M+H]+.

Workup

  1. temperatureThe resulting yellow solution was cooled with a ice-bath
  2. customthe temperature below 5° C
  3. customevaporated
  4. extractionThe resulting mixture was extracted with ethyl acetate
  5. washthe combined organic layers were then washed with water and brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customPurification by chromatography (SiO2, heptane:ethyl acetate:=100:0 to 7:3)

Sources & evidence

ORD record
ord-1048e235422045e7a2960d2eb01892ff
Source dataset
uspto-grants-2008_06
Patent number
US07388025B2

Reaction notes

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