Hydrochloric Acid → 5-(Bromomethyl)-1,2-oxazole-3-carboxylic acid

HRID 1409322Notes

Reaction equation

HRID 1409322 reaction equation
[Br:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]([O:10]CC)=[O:9])[CH:4]=1.[OH-].[Li+].Cl>C1COCC1.O>[Br:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]([OH:10])=[O:9])[CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 13124955Ethyl 5-(bromomethyl)-1,2-oxazole-3-carboxylate

Product 1

HCID 133710205-(Bromomethyl)-1,2-oxazole-3-carboxylic acidYield 61.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-(bromomethyl)isoxazole-3-carboxylate (4.27 mmol, 1 g) and lithium hydroxide (10.68 mmol, 0.256 g) were dissolved in THF (6.5 ml) and water (6.5 ml). The resulting mixture was stirred for 30 min at RT. The pH was adjusted to 4 with 1 M HCl and diluted with water. The mixture was extracted three times with EtOAc. The combined organics were dried, filtered and evaporated. 0.543 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 4.88 (s, 2H), 6.92 (s, 1H), 14.09 (bs, 1H).

Workup

  1. extractionThe mixture was extracted three times with EtOAc
  2. customThe combined organics were dried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-c0633ee8478b4fe383f2ecc11aa095d0
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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