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

HRID 1982432Notes

Reaction equation

HRID 1982432 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH3:14])[O:11][C:12]=2[CH3:13])=[CH:4][CH:3]=1.[Br:15]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:13][C:12]1[O:11][C:10]([CH3:14])=[N:9][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 11160071Oxazole, 4-(4-chlorophenyl)-2,5-dimethyl-

Product 1

HCID 132932935-(Bromomethyl)-4-(4-chlorophenyl)-2-methyl-1,3-oxazole

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 4-(4-chlorophenyl)-2,5-dimethyloxazole (6.21 g), N-bromosuccinimide (5.34 g) and azobisisobutyronitrile (0.25 g) in carbon tetrachloride (90 ml) was refluxed with stirring for 15 minutes, then 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 residue was crystallized from cold ethanol to give 5-bromomethyl-4-(4-chlorophenyl)-2-methyloxazole, yield 6.73 g (78.4%). Recrystallization from ethanol gave needles, melting at 75°-76° C.

Workup

  1. washwashed with water, saturated aqueous sodium hydrogen carbonate and water in that order
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationThe solvent was then distilled off
  4. customthe residue was crystallized from cold ethanol

Sources & evidence

ORD record
ord-39e7788ed2e845adb0303efd9a11125e
Source dataset
uspto-grants-1986_06
Patent number
US04596816

Reaction notes

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