1,3-Dibromo-5,5-dimethylhydantoin → 1-Bromoethyl ethyl carbonate

HRID 620449Notes

Reaction equation

HRID 620449 reaction equation
[C:1](=[O:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4].[Br:9]N1C(=O)C(C)(C)N(Br)C1=O.BrBr>C(Cl)(Cl)(Cl)Cl>[C:1](=[O:8])([O:5][CH:6]([Br:9])[CH3:7])[O:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 7766Diethyl CarbonateHCID 24408Bromine

Product 1

HCID 30215501-Bromoethyl ethyl carbonateYield 163.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of diethyl carbonate (35 g, 0.3 m) in carbon tetrachloride (50 ml) and alpha-azo-isobutyronitrile (AIBN) (0.1 g) was heated to gentle reflux and dibromodimethyl hydantoin (28.6 g, 0.1 m) was added in small aliquots over a period of 8 hours together with further additions of AIBN (8×0.05 g): care being taken to ensure that free bromine did not accumulate in the reaction mixture. At the end of the reaction the mixture was subjected to vacuum fractional distillation to afford pure ethyl alpha-bromoethyl carbonate (32.3 g, 82% yield) identical in all respects with the product of Examples 3 and 4.

Workup

  1. temperaturewas heated
  2. temperatureto gentle reflux
  3. customAt the end of the reaction the mixture
  4. distillationwas subjected to vacuum fractional distillation

Sources & evidence

ORD record
ord-18e71d6a23004e2f813419bcf8066203
Source dataset
uspto-grants-1989_04
Patent number
US04820857

Reaction notes

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