N-bromobutanimide → 5-Bromomethyl-2-phenylbenzoxazole

HRID 2120606

Reaction equation

HRID 2120606 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[N:7][C:6]=2[CH:16]=1.C1C(=O)N([Br:24])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:24][CH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[N:7][C:6]=2[CH:16]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 819192-Phenyl-5-methylbenzoxazole

Product 1

HCID 220628305-Bromomethyl-2-phenylbenzoxazoleYield 70.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

5-methyl-2-phenylbenzoxazole 55 (1.23 g, 5.8 mmol) and NBS (1.17 g, 6.5 mmol) were dissolved in carbon tetrachloride (20 ml). The mixture was evacuated and flushed with argon. AIBN (ca. 5 mg) was added and the mixture heated at reflux and irradiated with a sun lamp for 3 hrs. The solvent was evaporated under reduced pressure and the residue purified by chromatography to yield 1.18 g of 5-bromomethyl-2-phenylbenzoxazole 56.

Workup

  1. customThe mixture was evacuated
  2. customflushed with argon
  3. additionAIBN (ca. 5 mg) was added
  4. temperaturethe mixture heated
  5. temperatureat reflux
  6. customirradiated with a sun lamp for 3 hrs
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue purified by chromatography

Sources & evidence

ORD record
ord-a373492fe5344d06b44ae78302506fbc
Source dataset
uspto-grants-2004_02
Patent number
US06693098B2

Linked notes

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