Azobisisobutyronitrile → 5-(Bromomethyl)-2-methyl-4-phenyl-1,3-oxazole

HRID 1982421Notes

Reaction equation

HRID 1982421 reaction equation
[CH3:1][C:2]1[O:3][C:4]([CH3:13])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[Br:14]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:13][C:4]1[O:3][C:2]([CH3:1])=[N:6][C:5]=1[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 599323Oxazole, 2,5-dimethyl-4-phenyl-

Product 1

HCID 132932915-(Bromomethyl)-2-methyl-4-phenyl-1,3-oxazole

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2,5-dimethyl-4-phenyloxazole (6.0 g), N-bromosuccinimide (6.6 g), azobisisobutyronitrile (0.3 g) and carbon tetrachloride (120 ml) was refluxed with stirring for 5 minutes. The reaction mixture was washed with water, saturated aqueous sodium hydrogen carbonate and water in that order, and dried over anhydrous magnesium sulfate. The solvent was then distilled off and the oily residue was left standing to give 5-bromomethyl-2-methyl-4-phenyloxazole as crystals, yield 9.2 g (98.9%). Recrystallization from ethanol gave colorless needles, m.p. 80°-81° C.

Workup

  1. temperaturewas refluxed
  2. washThe reaction mixture was washed with water, saturated aqueous sodium hydrogen carbonate and water in that order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was then distilled off
  5. waitthe oily residue was left

Sources & evidence

ORD record
ord-edaac68b9b944d1187ac64009037a244
Source dataset
uspto-grants-1986_06
Patent number
US04596816

Reaction notes

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