Azobisisobutyronitrile → 6-(Bromomethyl)benzo[d]oxazole
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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.