Water → HCID 22261246, compound

HRID 348273Notes

Reaction equation

HRID 348273 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]([CH3:16])=[C:11]([CH2:13][C:14]#N)[N:12]=2)[CH:5]=[CH:6][CH:7]=1.COCCO.[OH-:22].[K+].[OH2:24]>>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]([CH3:16])=[C:11]([CH2:13][C:14]([OH:24])=[O:22])[N:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 962WaterHCID 80192-MethoxyethanolHCID 14797Potassium HydroxideHCID 22261181HCID 22261181, compound

Product 1

HCID 22261246HCID 22261246, compoundYield 60%

Procedure

The crude [2-(3-bromophenyl)-5-methyloxazole-4-yl]-acetonitrile (assume 0.22 mol) was combined with 2-methoxyethanol (630 mL) and 85% solid KOH (74.6 g, 1.33 mol) in water (360 mL) was added to the reaction. The mixture was heated to reflux for 3 h, cooled, quenched with 2 M HCl (500 mL), and extracted with CH2Cl2. The organic layer was dried (MgSO4), and the solvent removed in vacuo, using toluene to azeotropically remove residual 2-methoxyethanol. The crude product (57.3 g) was recrystallized from toluene (450 mL) to give 39.8 g (60%) of 2-(3-bromophenyl)-5-methyl-4-oxazoleacetic acid as an off-white powder.

Workup

  1. additionwas added to the reaction
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 3 h
  4. temperaturecooled
  5. customquenched with 2 M HCl (500 mL)
  6. extractionextracted with CH2Cl2
  7. dry with materialThe organic layer was dried (MgSO4)
  8. customthe solvent removed in vacuo
  9. customThe crude product (57.3 g) was recrystallized from toluene (450 mL)

Sources & evidence

ORD record
ord-40e53d3401734f41a8d5def5b70c28ba
Source dataset
uspto-grants-2007_02
Patent number
US07176224B2

Reaction notes

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