N-bromobutanimide → HCID 19697508, compound

HRID 1464796Notes

Reaction equation

HRID 1464796 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:6]=1.[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:12][CH2:1][C:2]1[O:3][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:6]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 12639612HCID 12639612, compound

Product 1

HCID 19697508HCID 19697508, compoundYield 65.7%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

111 mg of ethyl 2-methyloxazol-5-carboxylate [see J. Heterocyclic Chem., 17, 721 (1980)] was dissolved in 5 ml of carbon tetrachloride, 133 mg of N-bromosuccinimide and 5 mg of dibenzoyl peroxide was added. The mixture was refluxed for 3 hours under the irradiation of the artificial sun light, and then the solvent was evaporated. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=3/1] to give 110 mg of ethyl 2-bromomethyloxazole-5-carboxylate as a pale yellow oil.

Workup

  1. temperatureThe mixture was refluxed for 3 hours under the irradiation of the artificial sun light
  2. customthe solvent was evaporated
  3. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate=3/1]

Sources & evidence

ORD record
ord-b2288acc78084fdc9a8ba00f6342a90c
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

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