2-tert-Butyl-1,3-diisopropylisourea → tert-Butyl 3-bromo-2-oxobutanoate

HRID 616152Notes

Reaction equation

HRID 616152 reaction equation
[Br:1][CH:2]([CH3:8])[C:3](=[O:7])[C:4]([OH:6])=[O:5].[C:9](OC(=NC(C)C)NC(C)C)([CH3:12])([CH3:11])[CH3:10]>C(Cl)Cl>[Br:1][CH:2]([CH3:8])[C:3](=[O:7])[C:4]([O:6][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:5]

Participants

4

Reactant 2

HCID 110417822-tert-Butyl-1,3-diisopropylisoureaHCID 144712563-Bromo-2-oxobutanoic acid

Product 1

HCID 23470149tert-Butyl 3-bromo-2-oxobutanoateYield 47.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.6 g (8.85 mmol) of 3-bromo-2-ketobutyric acid and 7 g (4 equivalents) of O-t-butyl-N,N'-diisopropylpseudourea in 14 ml methylene chloride is stirred overnight at room temperature. After filtration, the solution is washed with NaHCO3 and brine, dried and evaporated to an oil which is chromatographed on silica gel with benzene as eluant to give 1 g (45%) of t-butyl 3-bromo-2-ketobutyrate.

Workup

  1. filtrationAfter filtration
  2. washthe solution is washed with NaHCO3 and brine
  3. customdried
  4. customevaporated to an oil which
  5. customis chromatographed on silica gel with benzene as eluant

Sources & evidence

ORD record
ord-c29cda835bc54ab8959fa3eeaf0abe29
Source dataset
uspto-grants-1978_02
Patent number
US04072674

Reaction notes

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