Bromine → Methyl 3-bromo-2-oxobutanoate

HRID 627696Notes

Reaction equation

HRID 627696 reaction equation
[O:1]=[C:2]([CH2:7][CH3:8])[C:3]([O:5][CH3:6])=[O:4].[Br:9]Br>C(Cl)Cl.CCOC(C)=O>[Br:9][CH:7]([CH3:8])[C:2](=[O:1])[C:3]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 2

HCID 24408BromineHCID 5451272-Ketobutyric acid methyl ester

Product 1

HCID 11183175Methyl 3-bromo-2-oxobutanoateYield 71.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-oxobutanoate (6.92 g, 59.6 mmol) in DCM (60 mL) at 0° C. was added bromine (3.10 mL, 60.3 mmol). The reaction mixture was warmed to room temperature and stirred for 2 h, diluted with EtOAc, washed with saturated NaHCO3 (2×), water (1×), brine (1×), dried over MgSO4, filtered, and concentrated. The product, methyl 3-bromo-2-oxobutanoate, (8.26 g, 42.4 mmol, 71% yield) was used in the next step without further purification.

Workup

  1. washwashed with saturated NaHCO3 (2×), water (1×), brine (1×)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-53f89b6dd3074dbba3ce21a497d9f73e
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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