1,3-Dibromo-5,5-dimethylhydantoin → 2-Bromo-1-ethyl-4-nitrobenzene

HRID 584298Notes

Reaction equation

HRID 584298 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1)[CH3:2].FC(F)(F)S(O)(=O)=O.[Br:20]N1C(C)(C)C(=O)N(Br)C1=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>ClCCl>[Br:20][C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[CH2:1][CH3:2]

Participants

6

Reactant 4

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 7480Benzene, 1-ethyl-4-nitro-HCID 24489Sodium DithioniteHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 223455942-Bromo-1-ethyl-4-nitrobenzeneYield 132.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

25 g (165 mmol) of 4-ethylnitrobenzene are placed in 200 ml of dichloromethane in a round-bottomed flask and under a stream of nitrogen. 20 ml (230 mmol) of trifluoromethanesulfonic acid and 33 g (115 mmol) of 1,3-dibromo-5,5-dimethylhydantoin are added and the reaction medium is stirred for 2 hours at room temperature. Saturated aqueous sodium hydrosulfite solution is then added. The phases are separated and the organic phase is neutralized with aqueous 2M sodium carbonate solution and then washed with water. It is then dried over magnesium sulfate, filtered and evaporated. 35 g (92%) of the expected product are obtained in the form of a yellow oil.

Workup

  1. customThe phases are separated
  2. washwashed with water
  3. dry with materialIt is then dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-2b59274e14724a06ae02d22b74338c58
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

Loading…