Azobisisobutyronitrile → 5-Bromomethyl-2-(4-methoxy-phenyl)-oxazole-4-carboxylic acid ethyl ester

HRID 2233563Notes

Reaction equation

HRID 2233563 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[O:9][C:10]=1[CH3:11])=[O:5])[CH3:2].N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:32]N1C(=O)CCC1=O>ClC(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[O:9][C:10]=1[CH2:11][Br:32])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 20064063Anticancer agent 73

Product 1

HCID 592961295-Bromomethyl-2-(4-methoxy-phenyl)-oxazole-4-carboxylic acid ethyl esterYield 135.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a boiling solution of 6.0 g 2-(4-methoxy-phenyl)-5-methyl-oxazole-4-carboxylic acid ethyl ester in 100 ml tetrachloro-methane were added portionwise a mixture of 1.51 g 2,2′-azobis(2-methylpropionitrile) and 4.9 g N-bromosuccinimide. The reaction mixture was refluxed for three hours. The cooled reaction mixture was filtered over a celite pad and the solvent removed in vacuo to obtain 10.6 g of crude 5-bromomethyl-2-(4-methoxy-phenyl)-oxazole-4-carboxylic acid ethyl ester, which contains to some extend the dibrominated byproduct. The material was used without further purification in the next step.

Workup

  1. temperatureThe reaction mixture was refluxed for three hours
  2. customThe cooled reaction mixture
  3. filtrationwas filtered over a celite pad
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-9f521d28e53f48188ed0cd8608f9a422
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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