Benzoyl Peroxide → HCID 67531220, compound

HRID 2388133Notes

Reaction equation

HRID 2388133 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:9][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:7][C:6]=1[CH3:16])=[O:4].[Br:17]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C1C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[O:9][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:7][C:6]=1[CH2:16][Br:17])=[O:4]

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 3310118methyl 4-methyl-2-phenyl-1,3-oxazole-5-carboxylate

Product 1

HCID 67531220HCID 67531220, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Methyl-2-phenyl-oxazole-5-carboxylic acid methyl ester (3.2 g, 14.7 mmol, prepared according to Cynkowski, T.; Cynkowska, G.; Ashton, P.; and Crooks, P. A. J. Chem. Soc., Chem. Commun. 1995, 2335), N-bromosuccinimide (2.69 g, 15.1 mmol), and benzoyl peroxide (356 mg, 1.47 mmol) were suspended in 37 mL of benzene and the mixture heated at reflux temperature for 16 hours. The reaction mixture was cooled and diluted with ethyl acetate. The mixture was washed successively with saturated bicarbonate solution, brine, saturated ammonium chloride solution, and brine. The organic solvent was dried, filtered, and concentrated. The crude product was purified by flash chromatography eluting from silica gel with a gradient of 0-40% ethyl acetate in hexanes to give 1.88 g of the title compound as a yellow solid. MS: (+) m/z 296.0, 298.0 (M+1, 79Br/81Br).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux temperature for 16 hours
  3. temperatureThe reaction mixture was cooled
  4. washThe mixture was washed successively with saturated bicarbonate solution, brine, saturated ammonium chloride solution, and brine
  5. customThe organic solvent was dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography
  9. washeluting from silica gel with a gradient of 0-40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-d02cd343206d40d2a939d799b9053d04
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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