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

HRID 2041220Notes

Reaction equation

HRID 2041220 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-a06ba3918baf403a9445e589a23cd135
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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