Bromine → 4-Bromo-2-(2,2,2-trichloroethoxycarbonylmethoxyimino)-3-oxobutyric acid

HRID 905425Notes

Reaction equation

HRID 905425 reaction equation
[Cl:1][C:2]([Cl:22])([Cl:21])[CH2:3][O:4][C:5]([CH2:7][O:8][N:9]=[C:10]([C:18](=[O:20])[CH3:19])[C:11]([O:13]C(C)(C)C)=[O:12])=[O:6].[Br:23]Br>C(O)(=O)C>[Br:23][CH2:19][C:18](=[O:20])[C:10](=[N:9][O:8][CH2:7][C:5]([O:4][CH2:3][C:2]([Cl:22])([Cl:21])[Cl:1])=[O:6])[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 24408BromineHCID 53973099Tert-butyl 2-(2,2,2-trichloroethoxycarbonylmethoxyimino)-3-oxobutyrate

Product 1

HCID 538664824-Bromo-2-(2,2,2-trichloroethoxycarbonylmethoxyimino)-3-oxobutyric acidYield 98.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of tert-butyl 2-(2,2,2-trichloroethoxycarbonylmethoxyimino)-3-oxobutyrate (29.5 g) in acetic acid (59 ml) was added bromine (23.2 g) at 52° C., and the mixture was stirred at 52° to 68° C. for 15 minutes. After removal of the acetic acid from the reaction mixture under reduced pressure, the residual oil was dissolved in ethyl acetate (400 ml). The solution was washed with 10% hydrochloric acid (20 ml) and a saturated aqueous sodium chloride, followed by drying over magnesium sulfate. Removal of the solvent gave 4-bromo-2-(2,2,2-trichloroethoxycarbonylmethoxyimino)-3-oxobutyric acid (30.7 g).

Workup

  1. customAfter removal of the acetic acid from the reaction mixture under reduced pressure
  2. dissolutionthe residual oil was dissolved in ethyl acetate (400 ml)
  3. washThe solution was washed with 10% hydrochloric acid (20 ml)
  4. dry with materialby drying over magnesium sulfate
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-67473aebe6004981a5ee76b9b4f6a502
Source dataset
uspto-grants-1983_12
Patent number
US04423213

Reaction notes

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