Azobisisobutyronitrile → 2-Bromomethyl-5-phenyl-benzoxazole

HRID 970809Notes

Reaction equation

HRID 970809 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:7][C:5]=2[N:6]=1.[Br:17]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 6547Azobisisobutyronitrile2×HCID 67184N-bromobutanimideHCID 112786Benzoxazole, 2-methyl-5-phenyl-

Product 1

HCID 151337542-Bromomethyl-5-phenyl-benzoxazoleYield 32.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-Methyl-5-phenyl-benzoxazole 48 (1.05 g, 5.0 mmol), N-bromosuccinimide (89 mg, 5.0 mmol) and azodiisobutyronitrile (AIBN) (41 mg, 0.25 mmol) in 1 ml of CCl4 was heated to reflux. After 5 hrs an additional 50 mg AIBN were added and the mixture was refluxed overnight. The mixture was diluted, washed with water, dried and concentrated. The crude product was chromatographed to give about 465 mg 2-bromomethyl-5-phenyl-benzoxazole 49.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. additionThe mixture was diluted
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe crude product was chromatographed

Sources & evidence

ORD record
ord-2d741824ac024329842d80a0c0ee3741
Source dataset
uspto-grants-2007_12
Patent number
US07312230B2

Reaction notes

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