Azobisisobutyronitrile → 2-Bromomethyl-5-phenyl-benzoxazole

HRID 1827988Notes

Reaction equation

HRID 1827988 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.CC(N=NC(C#N)(C)C)(C#N)C>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 azodilsobutyronitrile (AIBN) (41 mg, 0.25 mmol) in 10 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-c4a26a10b8d145d4b2c45d91623c8495
Source dataset
uspto-grants-2006_06
Patent number
US07056903B2

Reaction notes

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