Hydrochloric Acid → 5-(4-Bromophenyl)-3-methyl-1,2-oxazole-4-carboxylic acid

HRID 1253764Notes

Reaction equation

HRID 1253764 reaction equation
C[O:2][C:3]([C:5]1[C:6]([CH3:17])=[N:7][O:8][C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1)=[O:4].CO.[OH-].[Li+].Cl>O>[Br:16][C:13]1[CH:12]=[CH:11][C:10]([C:9]2[O:8][N:7]=[C:6]([CH3:17])[C:5]=2[C:3]([OH:4])=[O:2])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 56604575Methyl 5-(4-bromophenyl)-3-methylisoxazole-4-carboxylate

Product 1

HCID 566045595-(4-Bromophenyl)-3-methyl-1,2-oxazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carboxylic acid methyl ester (7.5 g, 25 mmol) was suspended in 2:1 methanol:water. Lithium hydroxide (2.1 g, 50 mmol) was added, and the reaction was stirred overnight at room temperature. The mixture was acidified to pH 1 with 1N aqueous HCl and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d5df3ccabb424e988c21ccd85defba1d
Source dataset
uspto-grants-2013_06
Patent number
US08455499B2

Reaction notes

Loading…