Water → Ethyl 5-(bromomethyl)-1,2-oxazole-3-carboxylate

HRID 1918511Notes

Reaction equation

HRID 1918511 reaction equation
Cl[C:2](=[N:8][OH:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Br:10][CH2:11][C:12]#[CH:13].C(=O)(O)[O-].[Na+].O>C(OCC)(=O)C>[Br:10][CH2:11][C:12]1[O:9][N:8]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 516892Sodium BicarbonateHCID 6816376Ethyl chloro(hydroximino)acetate

Product 1

HCID 13124955Ethyl 5-(bromomethyl)-1,2-oxazole-3-carboxylateYield 87.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of ethyl 2-chloro-2-(hydroxyimino)acetate (11 g; 70.41 mmol) in ethyl acetate (60 mL) was added dropwise at room temperature to a mixture of 3-bromoprop-1-yne (15.2 mL; 141 mmol), sodium bicarbonate (11.95 g; 141 mmol), ethyl acetate (400 mL), and water (4 mL). The mixture was stirred at room temperature for 24 h and the solid was removed by filtration and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel (eluent: 15 to 100% of dichloromethane in heptane) to give 14.38 g (87%) of ethyl 5-(bromomethyl)isoxazole-3-carboxylate as a white solid.

Workup

  1. customthe solid was removed by filtration
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by flash chromatography on silica gel (eluent: 15 to 100% of dichloromethane in heptane)

Sources & evidence

ORD record
ord-f9b9134b5e9d4b1e9c865a06f4d0d438
Source dataset
uspto-grants-2013_12
Patent number
US08618138B2

Reaction notes

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