Azobisisobutyronitrile → 5-(Bromomethyl)benzo[d]oxazole

HRID 911332Notes

Reaction equation

HRID 911332 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[N:7][C:6]=2[CH:10]=1.C1C(=O)N([Br:18])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)Cl>[Br:18][CH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[N:7][C:6]=2[CH:10]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27249705-Methylbenzoxazole

Product 1

HCID 219849815-(Bromomethyl)benzo[d]oxazoleYield 13%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Combine 5-methyl-benzoxazole (0.5 g, 3.75 mmol), NBS (0.7 g, 3.93 mmol), AIBN (60 mg, 0.37 mmol), chloroform (10 mL) and reflux for 1 h. Cool the reaction mixture to ambient temperature, dilute with chloroform and wash with water. Dry the organic extracts over anhydrous Na2SO4, evaporate the solvent and purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 4:1 and 7:3) to obtain the title compound as a white solid (0.1 g, 13%).

Workup

  1. washwash with water
  2. dry with materialDry the organic extracts over anhydrous Na2SO4
  3. customevaporate the solvent
  4. custompurify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 4:1 and 7:3)

Sources & evidence

ORD record
ord-f646cd2a66ad40a6ad4f41e201119d18
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

Loading…