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

HRID 1197820Notes

Reaction equation

HRID 1197820 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.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClC(Cl)(Cl)Cl>[Br:12][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 100%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a mixture of 6.2 parts of ethyl 5-methyl-2-oxazolecarboxylate and 191 parts of dry tetrachloromethane there were added 7.1 parts of N-bromosuccinimide and a few parts of benzoylperoxide under a nitrogen atmosphere. The whole was stirred for 1 hour at reflux temperature. After cooling, the reaction mixture was filtered and the filtrate was evaporated, yielding 11 parts (100%) of ethyl 5-(bromomethyl)-2-oxazolecarboxylate (interm. 21).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-47688e778e134fcea783de9728f0a9e5
Source dataset
uspto-grants-1994_01
Patent number
US05278165

Reaction notes

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