Acetic Acid → 5-(4-Bromophenyl)-1,2-oxazole-4-carboxylic acid

HRID 557683Notes

Reaction equation

HRID 557683 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][O:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)=[O:5])C.C(O)(=O)C.O>Cl>[Br:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]2[O:9][N:8]=[CH:7][C:6]=2[C:4]([OH:5])=[O:3])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 22220993Ethyl 5-(4-bromophenyl)isoxazole-4-carboxylate

Product 1

HCID 228317015-(4-Bromophenyl)-1,2-oxazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5-(4-Bromo-phenyl)-isoxazole-4-carboxylic acid ethyl ester (0.500 g, 1.69 mmol) was dissolved in concentrated hydrochloric acid (2 mL), acetic acid (5 mL), and H2O (5 mL), and the reaction was stirred at 100° C. overnight. The mixture was partitioned between EtOAc and H2O, and the organic layer was separated, dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. customThe mixture was partitioned between EtOAc and H2O
  2. customthe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-da65d1cc81da4a7f82813c2c6b8f288f
Source dataset
uspto-grants-2011_11
Patent number
US08058300B2

Reaction notes

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