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

HRID 58525

Reaction equation

HRID 58525 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-bb9378b602534687974a7e8d0a1bf5e2
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Linked notes

Loading…