Azobisisobutyronitrile → 6-(Bromomethyl)benzo[d]oxazole

HRID 1004317Notes

Reaction equation

HRID 1004317 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][O:8][C:4]=2[CH:3]=1.[Br:11]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)Cl>[Br:11][CH2:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27249696-Methylbenzoxazole

Product 1

HCID 219850576-(Bromomethyl)benzo[d]oxazoleYield 77.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 6-methylbenzoxazole (5.0 g; J. T. Gupton, K. F. Correia and B. S. Foster, Synthetic Communications, 1986, 16, 365), N-bromosuccinimide (7.0 g) and azobisisobutyronitrile (0.55 g) in dry chloroform (100 ml) was heated at reflux for 1 hour. The cooled reaction mixture was washed three times with water (40 ml), dried over magnesium sulphate and evaporated. The residual orange coloured viscous solid was triturated twice with pentane (50 ml) affording the title compound (6.20 g) as a buff coloured solid, m.p. 52-56° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. customThe cooled reaction mixture
  4. washwas washed three times with water (40 ml)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customwas triturated twice with pentane (50 ml)

Sources & evidence

ORD record
ord-73ba69673ea74b60b537ac0003fae1a0
Source dataset
uspto-grants-2000_04
Patent number
US06048893

Reaction notes

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