Reaction #927230

Reaction equation

t-Butyl ethyl malonate

1,3-dibromo-5,5-dimethylhydantoin

→

light yellow oil

Yield 176.5%

t-butyl ethyl bromomalonate

Yield 176.5%

Solvents

toluene

Conditions

Workup

1. 1
   TemperatureThe reaction was cooled
2. 2
   Concentrationconcentrated
3. 3
   WashThe organic layer was washed, with sat. NaHCO3 (2×), brine (3×)
4. 4
   Dryingdried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   OtherPurification
8. 8
   Filtrationby filtration on silica (70:30; hept:EtOAc)

Procedure

t-Butyl ethyl malonate (25.00 g, 0.13 mol) was dissolved in toluene and warmed to 80° C. To the resulting solution was added 1,3-dibromo-5,5-dimethylhydantoin (25.00 g, 0.07 mol). The reaction was stirred at elevated (80° C.) temperature 18 h. The reaction was cooled concentrated and taken up in Et2O. The organic layer was washed, with sat. NaHCO3 (2×), brine (3×), dried (MgSO4), filtered and concentrated. Purification by filtration on silica (70:30; hept:EtOAc) yielded 33.0 g (93%) of a light yellow oil. NMR and MS indicated a mixture of three compounds SM (20%), monobrominated (55%) and dibromonated diesters (25%). The material was used without further purification.

Source