Benzoyl Peroxide → Ethyl 5-(bromomethyl)oxazole-2-carboxylate

HRID 69090Notes

Reaction equation

HRID 69090 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:4][CH:3]=1.C1C(=O)N([Br:19])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:1][C:2]1[O:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 22099282Ethyl 5-methyl-1,3-oxazole-2-carboxylate

Product 1

HCID 19105062Ethyl 5-(bromomethyl)oxazole-2-carboxylateYield 62.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of ethyl 5-methyloxazole-2-carboxylate (5.1 g, 32.87 mmol) and NBS (8.19 g, 46.02 mmol) in carbon tetrachloride (50.0 mL), is added benzoyl peroxide (0.79 g, 3.29 mmol) and the reaction mixture is refluxed for 16 hours. The mixture is cooled to room temperature and filtered through diatomaceous earth. The filtrate is concentrated in vacuum and the crude is purified by silica gel chromatography, eluting with hexane:ethyl acetate (9.2:0.8) to give (4.8 g, 62.33%) of the title compound as a light brown oil. ESI/MS m/z (79Br/81Br) 234.1/236.1 [M+H]+.

Workup

  1. temperaturethe reaction mixture is refluxed for 16 hours
  2. filtrationfiltered through diatomaceous earth
  3. concentrationThe filtrate is concentrated in vacuum
  4. customthe crude is purified by silica gel chromatography
  5. washeluting with hexane:ethyl acetate (9.2:0.8)

Sources & evidence

ORD record
ord-caca7960d34249e383dc504078e6c4ea
Source dataset
uspto-grants-2014_09
Patent number
US08822486B2

Reaction notes

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