1,3-Dibromo-5,5-dimethylhydantoin → 1-Bromo-3,5-dinitrobenzene
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=1)([O-:3])=[O:2].[Br:13]N1C(C)(C)C(=O)N(Br)C1=O>S(=O)(=O)(O)O>[Br:13][C:8]1[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[C:6]([N+:10]([O-:12])=[O:11])[CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1,3-dinitrobenzene (25 g, 0.149 mol) in concentrated sulfuric acid (100 ml) at 0° C. was added 1,3-dibromo-5,5-dimethylhydantoin (31.75 g, 0.111 mol, 0.75 eq) portionwise over a period of 30 min. The mixture was stirred for 12 at RT and quenched by the addition of crushed ice. The precipitate formed was filtered and was washed repeatedly with water to obtain white solid. The solid was dried under vacuum to give the product in 87% yield (32 g).