Water → HCID 22261246, compound

HRID 2417033Notes

Reaction equation

HRID 2417033 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. 1H NMR (300 MHz, d6-DMSO) δ 7.99 (t, J=1.83 Hz, 1H), 7.88 (dt, J=8.1, 1.5 Hz, 1H), 7.65 (ddd, J=8.1, 1.8, 1.5 Hz, 1H), 7.45 (t, J=8.1 Hz, 1H), 3.50 (s, 2H), 2.35 (s, 3H).

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-c2840b1329c044a0bdb3cf69a3d945bc
Source dataset
uspto-grants-2004_11
Patent number
US06825222B2

Reaction notes

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